Intermolecular Carbonyl-Ene Approach to the Bicyclic Analogues of Enediyne Antibiotics, Neocarzinostatin, C-1027, and Kedarcidin: Highly Diastereoselective Carbonyl-Ene Reaction with an Alkyne-Cobalt Complex

Synlett

Volumn 1996, Issue 9, 1996, Pages 833-836

  Mikami, Koichi ^a   Feng, Feng ^a   Matsueda, Hiroyuki ^a   Yoshida, Akihiro ^a   Grierson, David S ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000743892     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5624     Document Type: Article

References (96)

1. Taken in part from the Ph. D. thesis of Hiroyuki Matsueda, Tokyo Institute of Technology, March, 1993 and the Master thesis of Feng Feng, Tokyo Institute of Technology, February, 1996.
2. Reviews: Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. Maier, M. E. Kontakte (Darmstadt) 1994, 2, 3. Lhermitte, H; Grierson, D. S. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Maier, M. E. Synlett 1995, 13. Hirama, M. J. Synth. Org. Chem., Jpn. 1991, 49, 1032. Toshima, K.; Nakata, M.; Matsumura, S. J. Synth. Org. Chem., Jpn. 1996, 54, 1032.
3. Reviews: Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. Maier, M. E. Kontakte (Darmstadt) 1994, 2, 3. Lhermitte, H; Grierson, D. S. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Maier, M. E. Synlett 1995, 13. Hirama, M. J. Synth. Org. Chem., Jpn. 1991, 49, 1032. Toshima, K.; Nakata, M.; Matsumura, S. J. Synth. Org. Chem., Jpn. 1996, 54, 1032.
4. Reviews: Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. Maier, M. E. Kontakte (Darmstadt) 1994, 2, 3. Lhermitte, H; Grierson, D. S. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Maier, M. E. Synlett 1995, 13. Hirama, M. J. Synth. Org. Chem., Jpn. 1991, 49, 1032. Toshima, K.; Nakata, M.; Matsumura, S. J. Synth. Org. Chem., Jpn. 1996, 54, 1032.
5. Reviews: Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. Maier, M. E. Kontakte (Darmstadt) 1994, 2, 3. Lhermitte, H; Grierson, D. S. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Maier, M. E. Synlett 1995, 13. Hirama, M. J. Synth. Org. Chem., Jpn. 1991, 49, 1032. Toshima, K.; Nakata, M.; Matsumura, S. J. Synth. Org. Chem., Jpn. 1996, 54, 1032.
6. Reviews: Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. Maier, M. E. Kontakte (Darmstadt) 1994, 2, 3. Lhermitte, H; Grierson, D. S. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Maier, M. E. Synlett 1995, 13. Hirama, M. J. Synth. Org. Chem., Jpn. 1991, 49, 1032. Toshima, K.; Nakata, M.; Matsumura, S. J. Synth. Org. Chem., Jpn. 1996, 54, 1032.
7. Reviews: Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. Maier, M. E. Kontakte (Darmstadt) 1994, 2, 3. Lhermitte, H; Grierson, D. S. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Maier, M. E. Synlett 1995, 13. Hirama, M. J. Synth. Org. Chem., Jpn. 1991, 49, 1032. Toshima, K.; Nakata, M.; Matsumura, S. J. Synth. Org. Chem., Jpn. 1996, 54, 1032.
8. Reviews: Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. Maier, M. E. Kontakte (Darmstadt) 1994, 2, 3. Lhermitte, H; Grierson, D. S. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Maier, M. E. Synlett 1995, 13. Hirama, M. J. Synth. Org. Chem., Jpn. 1991, 49, 1032. Toshima, K.; Nakata, M.; Matsumura, S. J. Synth. Org. Chem., Jpn. 1996, 54, 1032.
9. Reviews: Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. Maier, M. E. Kontakte (Darmstadt) 1994, 2, 3. Lhermitte, H; Grierson, D. S. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Maier, M. E. Synlett 1995, 13. Hirama, M. J. Synth. Org. Chem., Jpn. 1991, 49, 1032. Toshima, K.; Nakata, M.; Matsumura, S. J. Synth. Org. Chem., Jpn. 1996, 54, 1032.
10. Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot. 1965, 18, 68.
11. Excellent reviews: Goldberg, I. H. In Antibiotics; Hahn, F. H., Ed.; Springer-Verlag: Berlin, 1979; pp 262-274. Kappen, L. S.; Ellenberger, T. E.; Goldberg, I. H. Biochemistry 1987, 26, 384. Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191.
12. Excellent reviews: Goldberg, I. H. In Antibiotics; Hahn, F. H., Ed.; Springer-Verlag: Berlin, 1979; pp 262-274. Kappen, L. S.; Ellenberger, T. E.; Goldberg, I. H. Biochemistry 1987, 26, 384. Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191.
13. Excellent reviews: Goldberg, I. H. In Antibiotics; Hahn, F. H., Ed.; Springer-Verlag: Berlin, 1979; pp 262-274. Kappen, L. S.; Ellenberger, T. E.; Goldberg, I. H. Biochemistry 1987, 26, 384. Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191.
14. Koide, Y.; Ishii, F.; Hasuda, K.; Koyama, Y.; Edo, K.; Katamine, S.; Kitame, F.; Ishida, N. J. Antibiot. 1980, 33, 342. Kappen, L. S.; Napier, M. A.; Goldberg, I. H. Proc. Natl. Acad. Sci. U. S. A. 1980, 77, 1970.
15. Koide, Y.; Ishii, F.; Hasuda, K.; Koyama, Y.; Edo, K.; Katamine, S.; Kitame, F.; Ishida, N. J. Antibiot. 1980, 33, 342. Kappen, L. S.; Napier, M. A.; Goldberg, I. H. Proc. Natl. Acad. Sci. U. S. A. 1980, 77, 1970.
16. Myers, A. G. Tetrahedron Lett. 1987, 28, 4493. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212. Myers, A. G.; Harrington, P. M.; Kwon, B.-M. J. Am. Chem. Soc. 1992, 114, 1086. Myers, A. G.; Dragovich., P. S. J. Am. Chem. Soc. 1989, 111, 9130. Myers, A. G.; Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146. Myers, A. G.; Cohen, S. B.; Kwon, B.-M. J. Am. Chem. Soc. 1994, 116, 1670. Also see: Sugiyama, H.; Yamashita, K.; Nishi, M.; Saito, I. Tetrahedron Lett. 1992, 33, 515.
17. Myers, A. G. Tetrahedron Lett. 1987, 28, 4493. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212. Myers, A. G.; Harrington, P. M.; Kwon, B.-M. J. Am. Chem. Soc. 1992, 114, 1086. Myers, A. G.; Dragovich., P. S. J. Am. Chem. Soc. 1989, 111, 9130. Myers, A. G.; Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146. Myers, A. G.; Cohen, S. B.; Kwon, B.-M. J. Am. Chem. Soc. 1994, 116, 1670. Also see: Sugiyama, H.; Yamashita, K.; Nishi, M.; Saito, I. Tetrahedron Lett. 1992, 33, 515.
18. Myers, A. G. Tetrahedron Lett. 1987, 28, 4493. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212. Myers, A. G.; Harrington, P. M.; Kwon, B.-M. J. Am. Chem. Soc. 1992, 114, 1086. Myers, A. G.; Dragovich., P. S. J. Am. Chem. Soc. 1989, 111, 9130. Myers, A. G.; Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146. Myers, A. G.; Cohen, S. B.; Kwon, B.-M. J. Am. Chem. Soc. 1994, 116, 1670. Also see: Sugiyama, H.; Yamashita, K.; Nishi, M.; Saito, I. Tetrahedron Lett. 1992, 33, 515.
19. Myers, A. G. Tetrahedron Lett. 1987, 28, 4493. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212. Myers, A. G.; Harrington, P. M.; Kwon, B.-M. J. Am. Chem. Soc. 1992, 114, 1086. Myers, A. G.; Dragovich., P. S. J. Am. Chem. Soc. 1989, 111, 9130. Myers, A. G.; Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146. Myers, A. G.; Cohen, S. B.; Kwon, B.-M. J. Am. Chem. Soc. 1994, 116, 1670. Also see: Sugiyama, H.; Yamashita, K.; Nishi, M.; Saito, I. Tetrahedron Lett. 1992, 33, 515.
20. Myers, A. G. Tetrahedron Lett. 1987, 28, 4493. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212. Myers, A. G.; Harrington, P. M.; Kwon, B.-M. J. Am. Chem. Soc. 1992, 114, 1086. Myers, A. G.; Dragovich., P. S. J. Am. Chem. Soc. 1989, 111, 9130. Myers, A. G.; Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146. Myers, A. G.; Cohen, S. B.; Kwon, B.-M. J. Am. Chem. Soc. 1994, 116, 1670. Also see: Sugiyama, H.; Yamashita, K.; Nishi, M.; Saito, I. Tetrahedron Lett. 1992, 33, 515.
21. Myers, A. G. Tetrahedron Lett. 1987, 28, 4493. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212. Myers, A. G.; Harrington, P. M.; Kwon, B.-M. J. Am. Chem. Soc. 1992, 114, 1086. Myers, A. G.; Dragovich., P. S. J. Am. Chem. Soc. 1989, 111, 9130. Myers, A. G.; Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146. Myers, A. G.; Cohen, S. B.; Kwon, B.-M. J. Am. Chem. Soc. 1994, 116, 1670. Also see: Sugiyama, H.; Yamashita, K.; Nishi, M.; Saito, I. Tetrahedron Lett. 1992, 33, 515.
22. Myers, A. G. Tetrahedron Lett. 1987, 28, 4493. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212. Myers, A. G.; Harrington, P. M.; Kwon, B.-M. J. Am. Chem. Soc. 1992, 114, 1086. Myers, A. G.; Dragovich., P. S. J. Am. Chem. Soc. 1989, 111, 9130. Myers, A. G.; Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146. Myers, A. G.; Cohen, S. B.; Kwon, B.-M. J. Am. Chem. Soc. 1994, 116, 1670. Also see: Sugiyama, H.; Yamashita, K.; Nishi, M.; Saito, I. Tetrahedron Lett. 1992, 33, 515.
23. Mayer, J.; Sondheimer, F. J. Am. Chem. Soc. 1966, 88, 602. Darby, N.; Kim, C. U.; Salaun, J. A.; Shelton, K. W.; Takada, S.; Masamune, S. J. Chem. Soc., Chem. Commun. 1971, 1561. Jones, R. R.; Bergmann, R. G. J. Am. Chem. Soc. 1972, 94, 660. Bergmann, R. G. Acc. Chem. Res. 1973, 6, 25. Wong, H. N. C.; Sondheimer, F. Tetrahedron Lett. 1980, 21, 217.
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25. Mayer, J.; Sondheimer, F. J. Am. Chem. Soc. 1966, 88, 602. Darby, N.; Kim, C. U.; Salaun, J. A.; Shelton, K. W.; Takada, S.; Masamune, S. J. Chem. Soc., Chem. Commun. 1971, 1561. Jones, R. R.; Bergmann, R. G. J. Am. Chem. Soc. 1972, 94, 660. Bergmann, R. G. Acc. Chem. Res. 1973, 6, 25. Wong, H. N. C.; Sondheimer, F. Tetrahedron Lett. 1980, 21, 217.
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27. Mayer, J.; Sondheimer, F. J. Am. Chem. Soc. 1966, 88, 602. Darby, N.; Kim, C. U.; Salaun, J. A.; Shelton, K. W.; Takada, S.; Masamune, S. J. Chem. Soc., Chem. Commun. 1971, 1561. Jones, R. R.; Bergmann, R. G. J. Am. Chem. Soc. 1972, 94, 660. Bergmann, R. G. Acc. Chem. Res. 1973, 6, 25. Wong, H. N. C.; Sondheimer, F. Tetrahedron Lett. 1980, 21, 217.
28. Dasgupta, D.; Goldberg, I. H. Biochemistry 1985, 24, 6913. Kappen, L. S.; Ellenberger, T. E.; Goldberg, I. H. Proc. Biochemistry 1987, 26, 383.
29. Dasgupta, D.; Goldberg, I. H. Biochemistry 1985, 24, 6913. Kappen, L. S.; Ellenberger, T. E.; Goldberg, I. H. Proc. Biochemistry 1987, 26, 383.
30. Kedarcidin: Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. L̇eet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1991, 44, 472. C-1027: Hu, J.; Xue, Y.-C.; Xie, M.-Y; Zhang, R.; Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T. J. Antibiot. 1988, 41, 1575. Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T.; Zhang, R.; Xie, M-Y. J. Antibiot. 1988, 41, 1580. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T., Tetrahedron Lett. 1993, 34, 2633. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Sugiura, Y.; Matsumoto, T. Biochemistry 1993, 32, 5548.
31. Kedarcidin: Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. L̇eet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1991, 44, 472. C-1027: Hu, J.; Xue, Y.-C.; Xie, M.-Y; Zhang, R.; Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T. J. Antibiot. 1988, 41, 1575. Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T.; Zhang, R.; Xie, M-Y. J. Antibiot. 1988, 41, 1580. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T., Tetrahedron Lett. 1993, 34, 2633. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Sugiura, Y.; Matsumoto, T. Biochemistry 1993, 32, 5548.
32. Kedarcidin: Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. L̇eet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1991, 44, 472. C-1027: Hu, J.; Xue, Y.-C.; Xie, M.-Y; Zhang, R.; Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T. J. Antibiot. 1988, 41, 1575. Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T.; Zhang, R.; Xie, M-Y. J. Antibiot. 1988, 41, 1580. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T., Tetrahedron Lett. 1993, 34, 2633. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Sugiura, Y.; Matsumoto, T. Biochemistry 1993, 32, 5548.
33. Kedarcidin: Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. L̇eet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1991, 44, 472. C-1027: Hu, J.; Xue, Y.-C.; Xie, M.-Y; Zhang, R.; Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T. J. Antibiot. 1988, 41, 1575. Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T.; Zhang, R.; Xie, M-Y. J. Antibiot. 1988, 41, 1580. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T., Tetrahedron Lett. 1993, 34, 2633. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Sugiura, Y.; Matsumoto, T. Biochemistry 1993, 32, 5548.
34. Kedarcidin: Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. L̇eet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1991, 44, 472. C-1027: Hu, J.; Xue, Y.-C.; Xie, M.-Y; Zhang, R.; Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T. J. Antibiot. 1988, 41, 1575. Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T.; Zhang, R.; Xie, M-Y. J. Antibiot. 1988, 41, 1580. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T., Tetrahedron Lett. 1993, 34, 2633. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Sugiura, Y.; Matsumoto, T. Biochemistry 1993, 32, 5548.
35. Kedarcidin: Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. L̇eet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1991, 44, 472. C-1027: Hu, J.; Xue, Y.-C.; Xie, M.-Y; Zhang, R.; Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T. J. Antibiot. 1988, 41, 1575. Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T.; Zhang, R.; Xie, M-Y. J. Antibiot. 1988, 41, 1580. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T., Tetrahedron Lett. 1993, 34, 2633. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Sugiura, Y.; Matsumoto, T. Biochemistry 1993, 32, 5548.
36. Kedarcidin: Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. L̇eet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1991, 44, 472. C-1027: Hu, J.; Xue, Y.-C.; Xie, M.-Y; Zhang, R.; Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T. J. Antibiot. 1988, 41, 1575. Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T.; Zhang, R.; Xie, M-Y. J. Antibiot. 1988, 41, 1580. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T., Tetrahedron Lett. 1993, 34, 2633. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Sugiura, Y.; Matsumoto, T. Biochemistry 1993, 32, 5548.
37. Kedarcidin: Lam, K. S.; Hesler, G. A.; Gustavson, D. R.; Crosswell, A. R.; Veitch, J. M.; Forenza, S.; Tomita, K. J. Antibiot. 1991, 44, 472. L̇eet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquardt, H. J. Antibiot. 1991, 44, 472. C-1027: Hu, J.; Xue, Y.-C.; Xie, M.-Y; Zhang, R.; Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T. J. Antibiot. 1988, 41, 1575. Otani, T.; Minami, Y.; Yamada, Y.; Marunaka, T.; Zhang, R.; Xie, M-Y. J. Antibiot. 1988, 41, 1580. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T., Tetrahedron Lett. 1993, 34, 2633. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Sugiura, Y.; Matsumoto, T. Biochemistry 1993, 32, 5548.
38. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
39. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
40. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
41. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
42. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
43. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
44. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
45. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
46. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
47. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
48. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
49. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
50. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.;
51. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
52. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
53. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
54. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
55. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
56. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
57. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
58. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
59. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
60. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
61. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
62. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
63. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
64. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
65. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
66. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
67. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
68. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991,
69. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
70. For the previous syntheses, see the comprehensive review (ref. 2). Also see: carbonyl addition of acetylide: (a) Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. (b) Danishefsky, S. J.; Mantlo, N. B.; Yamashita, D. S. J. Am. Chem. Soc. 1988, 110, 6890. Haseltine, J. N.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 7638. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850. (c) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694. (d) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. (e) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619. (f) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310; 1995, 117, 8875. carbonyl addition of allylic metal: (g) Wender, P. A.; McKinney, J. A.; Mukai, C. J. Am. Chem Soc. 1990, 112, 5369. thioetherificalion: (h) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114 , 7360. (i) Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. J. Am. Chem. Soc. 1988, 110, 7247. (J) Nicolaou, K. C.; Skokotas, G.; Maligres, P.; Zuccarello, G.; Schweiger, E. J.; Toshima, K.; Wendeborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272. (k) Toshima, K.; Ohta, T.; Ohtake, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 391. Toshima, K.; Ohta, T.; Ohashi, A.; Nakamura, T.; Nakata, M.; Tatsuta, K.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 4822. (l) Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 52, 4363. thioetherification-ring contraction: (m) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Diels-Alder reaction: (n) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. enolate alkylation with alkyne-cobalt complex: (o) Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921. Magnus, P.; Pitterna, T. J. Chem. Soc., Chem. Commun. 1991, 541; 1991, 1552. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283. (p) Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851. Pd-catalyzed coupling reaction: (q) Hirama, M.; Fujiwara, K.; Shigematsu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120. Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. Fujiwara, K. Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688. etherification and then the [2,3]Wittig ring contraction: (r) Doi, T.; Takahashi, T. J. Org. Chem. 1991, 56, 3465. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem. Int., Ed. Engl. 1995, 34, 1345. (s) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 4563. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Chiaroni, A.; Riche, C.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Ulibarri, G; Nadler, W; Skyrydstrup, T.; Audrain, H.; Riche, C.; Chiaroni, A.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753 and references cited therein. However, there has been no approach based on the ene reaction except for our intramolecular carbonyl-ene strategy (ref. 12).
71. For the previous synthesis of monocyclic analogues: (a) Nakatani, K.; Arai, K.; Yamada, K.; Terashima, S. Tetrahedron Lett. 1990, 31, 2323. Nakatani, K.; Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1992, 48, 633. Nakatani, K. Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1993, 34, 2139. (b) Suffert, J.; Bruckner, R. Tetrahedron Lett. 1991, 32, 1453. Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 52, 1449. (c) Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A.; Heravi, M. H. Tetrahedron Lett. 1990, 31, 2323. (d) Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991.
72. For the previous synthesis of monocyclic analogues: (a) Nakatani, K.; Arai, K.; Yamada, K.; Terashima, S. Tetrahedron Lett. 1990, 31, 2323. Nakatani, K.; Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1992, 48, 633. Nakatani, K. Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1993, 34, 2139. (b) Suffert, J.; Bruckner, R. Tetrahedron Lett. 1991, 32, 1453. Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 52, 1449. (c) Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A.; Heravi, M. H. Tetrahedron Lett. 1990, 31, 2323. (d) Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991.
73. For the previous synthesis of monocyclic analogues: (a) Nakatani, K.; Arai, K.; Yamada, K.; Terashima, S. Tetrahedron Lett. 1990, 31, 2323. Nakatani, K.; Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1992, 48, 633. Nakatani, K. Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1993, 34, 2139. (b) Suffert, J.; Bruckner, R. Tetrahedron Lett. 1991, 32, 1453. Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 52, 1449. (c) Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A.; Heravi, M. H. Tetrahedron Lett. 1990, 31, 2323. (d) Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991.
74. For the previous synthesis of monocyclic analogues: (a) Nakatani, K.; Arai, K.; Yamada, K.; Terashima, S. Tetrahedron Lett. 1990, 31, 2323. Nakatani, K.; Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1992, 48, 633. Nakatani, K. Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1993, 34, 2139. (b) Suffert, J.; Bruckner, R. Tetrahedron Lett. 1991, 32, 1453. Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 52, 1449. (c) Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A.; Heravi, M. H. Tetrahedron Lett. 1990, 31, 2323. (d) Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991.
75. For the previous synthesis of monocyclic analogues: (a) Nakatani, K.; Arai, K.; Yamada, K.; Terashima, S. Tetrahedron Lett. 1990, 31, 2323. Nakatani, K.; Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1992, 48, 633. Nakatani, K. Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1993, 34, 2139. (b) Suffert, J.; Bruckner, R. Tetrahedron Lett. 1991, 32, 1453. Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 52, 1449. (c) Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A.; Heravi, M. H. Tetrahedron Lett. 1990, 31, 2323. (d) Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991.
76. For the previous synthesis of monocyclic analogues: (a) Nakatani, K.; Arai, K.; Yamada, K.; Terashima, S. Tetrahedron Lett. 1990, 31, 2323. Nakatani, K.; Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1992, 48, 633. Nakatani, K. Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1993, 34, 2139. (b) Suffert, J.; Bruckner, R. Tetrahedron Lett. 1991, 32, 1453. Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 52, 1449. (c) Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A.; Heravi, M. H. Tetrahedron Lett. 1990, 31, 2323. (d) Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991.
77. For the previous synthesis of monocyclic analogues: (a) Nakatani, K.; Arai, K.; Yamada, K.; Terashima, S. Tetrahedron Lett. 1990, 31, 2323. Nakatani, K.; Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1992, 48, 633. Nakatani, K. Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1993, 34, 2139. (b) Suffert, J.; Bruckner, R. Tetrahedron Lett. 1991, 32, 1453. Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 52, 1449. (c) Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A.; Heravi, M. H. Tetrahedron Lett. 1990, 31, 2323. (d) Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991.
78. For our intramolecular carbonyl-ene approach, see: Mikami, K.; Matsueda, H.; Nakai, T. Tetrahedron Lett. 1993, 34, 3571; Synlett 1993, 23. However, in our intramolecular carbonyl-ene reaction, the carbonyl-ene product could not be isolated under thermal ene reaction conditions and the dehydrated (or further transformed) product was obtained.
79. For our intramolecular carbonyl-ene approach, see: Mikami, K.; Matsueda, H.; Nakai, T. Tetrahedron Lett. 1993, 34, 3571; Synlett 1993, 23. However, in our intramolecular carbonyl-ene reaction, the carbonyl-ene product could not be isolated under thermal ene reaction conditions and the dehydrated (or further transformed) product was obtained.
80. For the carbonyl-ene reaction with conjugated ynals as reactive enophiles, see: Mikami, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1988, 1430.
81. 11b (15) For the use of alkoxy(methyl)aluminum chloride as a Lewis acid for carbonyl-ene reaction, see ref. 13.
82. -1.
83. Nicholas, K. M. Acc. Chem. Res. 1973, 6, 26. Nicholas, K. M.; Mulraney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128. Schreiber, S. L.; Klimas, M. Y.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1987, 109, 5749.
84. Nicholas, K. M. Acc. Chem. Res. 1973, 6, 26. Nicholas, K. M.; Mulraney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128. Schreiber, S. L.; Klimas, M. Y.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1987, 109, 5749.
85. Nicholas, K. M. Acc. Chem. Res. 1973, 6, 26. Nicholas, K. M.; Mulraney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128. Schreiber, S. L.; Klimas, M. Y.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1987, 109, 5749.
86. Nicholas, K. M. Acc. Chem. Res. 1973, 6, 26. Nicholas, K. M.; Mulraney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128. Schreiber, S. L.; Klimas, M. Y.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1987, 109, 5749.
87. Quite recently, Suzuki et al. reported the use of cobalt complex of 2-(α-alkynyl)propene as a reactive ene donor: Nagasawa, T.; Kitamura, M.; Suzuki, K. Synlett 1995, 1183.
88. -1.
89. For the general discussion on the erythro-diastereoselectivity for the carbonyl-ene reaction with conjugated ynals, see ref. 13.
90. Hanaoka et al. reported a high diastereoselectivity in the aldol reaction with cobalt complex of 3-(trimethylsilyl)propynal as the aldehyde: Mukai, C.; Suzuki, K.; Nagami, K.; Hanaoka, M. J. Chem. Soc., Perkin Trans. 1 1992, 141. Mukai, C.; Kataoka, O.; Hanaoka, M. J. Chem. Soc., Perkin Trans, 1 1993, 563.
91. Hanaoka et al. reported a high diastereoselectivity in the aldol reaction with cobalt complex of 3-(trimethylsilyl)propynal as the aldehyde: Mukai, C.; Suzuki, K.; Nagami, K.; Hanaoka, M. J. Chem. Soc., Perkin Trans. 1 1992, 141. Mukai, C.; Kataoka, O.; Hanaoka, M. J. Chem. Soc., Perkin Trans, 1 1993, 563.
92. The bonding of the normally linear sp-hybridized acetylene triple bond is released to approximately 145 °.
93. 3 (basic, 49 g) followed by solvent removal under vacuum according to the ref. 10j.
94. 12OS 204.0610, found 204.0598.
95. Chem. Eng. News. 1995, August 28th Issue, 28.
96. 2 256.1464, found 256.1452.