β-alkoxycarbonyl enol triflates as precursors of stereopure 3-ene-1,5- diyne building blocks for the chromophores of neocarzinostatin, C-1027, kedarcidin, maduropeptin, and N1999A2

Synthesis

Volumn , Issue 4, 2000, Pages 588-602

  Gebauer, Olaf ^a   Brückner, Reinhard ^b,c  

^a BAYER AG   (Germany)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

^c UNIVERSITY OF FREIBURG   (Germany)

Author keywords

C C couplings; Enediynes; Enynes; Stereoselective enolate formation; oxo esters

Indexed keywords

ALDEHYDE; ANTIBIOTIC C 1027; ESTER; KEDARCIDIN; TRIFLUOROMETHANESULFONIC ACID; ZINOSTATIN;

CHEMICAL REACTION; CHROMATOPHORE; DRUG CONFORMATION; DRUG SYNTHESIS; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 19244375698     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6366     Document Type: Review

References (69)

1. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
2. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
3. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
4. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
5. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
6. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
7. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
8. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
9. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
10. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
11. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
12. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
13. Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 211. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. Lee, M. D.; Ellestadt, A. G.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235; Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Maier, M. E. Kontakte (Merck) 1994, 2, 3; Synlett 1995, 13. Nicolaou, K. C.; Smith A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F.Eds.; VCH-Verlagsgesellschaft: Weinheim 1995, 203-283. Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 41; 1996, 3, 93. Wang, K. K. Chem. Rev. 1996, 96, 207. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. Brückner, R.; Suffert, J. Synlett 1999, 657.
14. Golik, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.-I.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3462.
15. Lee, M. D.; Dunne, T.-S.; Chang, C. C.; Ellestad, G. A.; Siegel, M. M.; Morton, G. O.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3466.
16. Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1990, 112, 3715.
17. Leet, 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. Revised structure: Kawata, S.; Ashizawa, S.; Hirama, M. J. Am. Chem. Soc. 1997, 119, 12012.
18. Leet, 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. Revised structure: Kawata, S.; Ashizawa, S.; Hirama, M. J. Am. Chem. Soc. 1997, 119, 12012.
19. Yoshida, K.-i.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637.
20. Schroeder, D. R.; Colson, K. L.; Klohr, S. E.; Zein, N.; Langley, D. R.; Lee, M. S.; Matson, J. A.; Doyle, T. W. J. Am. Chem. Soc. 1994, 116, 9351.
21. Koide, Y.; Ishi, F.; Hasuda, K.; Koyama, Y.; Edo, K.; Katamine, S.; Kitame, F.; Ishida, N. J. Antibiot. 1980, 33, 342 Edo, K.; Katamine, S.; Kitame, F.; Ishida, N.; Koide, Y.; Kusano, G.; Nozoe, S. J. Antibiot. 1980, 33, 347 (partially revised in Shibuya, M.; Toyooka, K.; Kubota, S. Tetrahedron Lett. 1984, 25, 1171). Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
22. Koide, Y.; Ishi, F.; Hasuda, K.; Koyama, Y.; Edo, K.; Katamine, S.; Kitame, F.; Ishida, N. J. Antibiot. 1980, 33, 342 Edo, K.; Katamine, S.; Kitame, F.; Ishida, N.; Koide, Y.; Kusano, G.; Nozoe, S. J. Antibiot. 1980, 33, 347 (partially revised in Shibuya, M.; Toyooka, K.; Kubota, S. Tetrahedron Lett. 1984, 25, 1171). Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
23. Koide, Y.; Ishi, F.; Hasuda, K.; Koyama, Y.; Edo, K.; Katamine, S.; Kitame, F.; Ishida, N. J. Antibiot. 1980, 33, 342 Edo, K.; Katamine, S.; Kitame, F.; Ishida, N.; Koide, Y.; Kusano, G.; Nozoe, S. J. Antibiot. 1980, 33, 347 (partially revised in Shibuya, M.; Toyooka, K.; Kubota, S. Tetrahedron Lett. 1984, 25, 1171). Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
24. Koide, Y.; Ishi, F.; Hasuda, K.; Koyama, Y.; Edo, K.; Katamine, S.; Kitame, F.; Ishida, N. J. Antibiot. 1980, 33, 342 Edo, K.; Katamine, S.; Kitame, F.; Ishida, N.; Koide, Y.; Kusano, G.; Nozoe, S. J. Antibiot. 1980, 33, 347 (partially revised in Shibuya, M.; Toyooka, K.; Kubota, S. Tetrahedron Lett. 1984, 25, 1171). Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
25. Koide, Y.; Ishi, F.; Hasuda, K.; Koyama, Y.; Edo, K.; Katamine, S.; Kitame, F.; Ishida, N. J. Antibiot. 1980, 33, 342 Edo, K.; Katamine, S.; Kitame, F.; Ishida, N.; Koide, Y.; Kusano, G.; Nozoe, S. J. Antibiot. 1980, 33, 347 (partially revised in Shibuya, M.; Toyooka, K.; Kubota, S. Tetrahedron Lett. 1984, 25, 1171). Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
26. Ando, T.; Ishii, M.; Kajiura, T.; Kameyama, T.; Miwa, K.; Suguira, Y. Tetrahedron Lett. 1998, 39, 6495.
27. Myers, A. G.; Alauddin, M. M.; Fuhry, M. M.; Dragovich, P. S.; Finney, N. S.; Harrington, P. M. Tetrahedron Lett. 1989, 30, 6997.
28. Myers, A. G.; Hammond, M.; Wu, Y.; Xiang, J. N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006-Myers, A. G.; Liang, J.; Hammond, M.; Harrington, P. M.; Wu, Y.; Kuo, E. Y. J. Am. Chem. Soc. 1998, 120, 5319.
29. Myers, A. G.; Hammond, M.; Wu, Y.; Xiang, J. N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006-Myers, A. G.; Liang, J.; Hammond, M.; Harrington, P. M.; Wu, Y.; Kuo, E. Y. J. Am. Chem. Soc. 1998, 120, 5319.
30. Dai, W.-M.; Fong, K. C. Tetrahedron Lett. 1996, 37, 8413.
31. Method: Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rüther, G. J. Am. Chem. Soc. 1997, 119, 698. Trost, B. M.; McIntosh, M. C. Tetrahedron Lett. 1997, 38, 3207.
32. Method: Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rüther, G. J. Am. Chem. Soc. 1997, 119, 698. Trost, B. M.; McIntosh, M. C. Tetrahedron Lett. 1997, 38, 3207.
33. Trost, B. M.; Hachiya, I.; McIntosh, M. C. Tetrahedron Lett. 1998, 39, 6445.
34. Synthesis applications of enol triflates were reviewed by Ritter, K. Synthesis 1993, 735.
35. Method: Cacchi, S.; Morera, E.; Ortar, G. Synthesis 1986, 320. For related couplings with alkenyl halide cf. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
36. Method: Cacchi, S.; Morera, E.; Ortar, G. Synthesis 1986, 320. For related couplings with alkenyl halide cf. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
37. Cf. the reaction 12→13 in Eis, K.; Schmalz, H.-G. Synthesis 1997, 202.
38. Aldercide, M.; Spino, C.; Weiler, L. Tetrahedron Lett. 1984, 25, 1643.
39. a) Certain β-oxo aldehydes were converted in a very similar manner into stereopure enol triflates with Z-selectivity when a lithium enolate (in THF) was the intermediate or with E-selectivity via the 2,6-di-tert-butylpyridinium enolate (in dichloromethane): Brückner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 32, 1449. Suffert, J.; Brückner, R. Tetrahedron Lett. 1991, 32, 1453. K. Brickmann, F. Hambloch, J. Suffert, R. Brückner, Liebigs Ann. 1996, 457.
40. a) Certain β-oxo aldehydes were converted in a very similar manner into stereopure enol triflates with Z-selectivity when a lithium enolate (in THF) was the intermediate or with E-selectivity via the 2,6-di-tert-butylpyridinium enolate (in dichloromethane): Brückner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 32, 1449. Suffert, J.; Brückner, R. Tetrahedron Lett. 1991, 32, 1453. K. Brickmann, F. Hambloch, J. Suffert, R. Brückner, Liebigs Ann. 1996, 457.
41. a) Certain β-oxo aldehydes were converted in a very similar manner into stereopure enol triflates with Z-selectivity when a lithium enolate (in THF) was the intermediate or with E-selectivity via the 2,6-di-tert-butylpyridinium enolate (in dichloromethane): Brückner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 32, 1449. Suffert, J.; Brückner, R. Tetrahedron Lett. 1991, 32, 1453. K. Brickmann, F. Hambloch, J. Suffert, R. Brückner, Liebigs Ann. 1996, 457.
42. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
43. Crisp, G. T.; Meyer, A. G. J. Org. Chem. 1992, 57, 6972.
44. Keenan, R. M.; Weinstock, J.; Finkelstein, J. A.; Franz, R. G.; Gaitanopoulos, D. E.; Girard, G. R.; Hill, D. T.; Morgan, T. M.; Samanen, J. M.; Hempel, J.; Eggleston, D. S.; Ayar, N.; Griffin, E.; Ohlstein, E. H.; Stack, E. J.; Weidley, E. F.; Edwards, R. J. J. Med. Chem. 1992, 35, 3858.
45. Görth, F. C.; Brückner, R. Synthesis 1999, 1520.
46. Method: Huang, S. L.; Omura, K.; Swern, D. J. Org. Chem. 1976, 41, 3329.
47. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258.
48. a) Reimnitz, F. Diplomarbeit, Universität Göttingen 1996.
49. b) Schmid, C. R.; Bryant, J. D.; Dowlatzedah, M.; Phillips, J. L.; Prather, D. E.; Schantz, R. R.; Sear, N. L.; Vianco, C. S. J. Org. Chem. 1991, 56, 4056.
50. Tipson, R. S.; Cohen, A. Carbohydr. Res. 1968, 7, 237.
51. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
52. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
53. Garner, P.; Park, J. M. Org. Synth. 1992, 70, 18.
54. Houpis, I. N. Tetrahedron Lett. 1991, 32, 6675.
55. Comins, D. A.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
56. Kant, J.; Roth, J. A.; Fuller, C. E.; Walker, D. G.; Benigni, D. A.; Farina, V. J. Org. Chem. 1994, 59, 4956.
57. a) Gibbs, R. A.; Krishnan, U.; Dolence, J. M.; Poulter, C. D. J. Org. Chem. 1995, 60, 7821.
58. 3Sn-C≡C-H under and destannylated thereafter to obtain 31% of the derived Z-enyne.
59. Original procedure: Ramirez, F.; Desai, N. B.; Mc Kelvie, N. J. Am. Chem. Soc. 1962, 84, 1745. Extension thereof: Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
60. Original procedure: Ramirez, F.; Desai, N. B.; Mc Kelvie, N. J. Am. Chem. Soc. 1962, 84, 1745. Extension thereof: Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
61. Regitz, M.; Anschütz, W. Liebigs Ann. Chem. 1969, 730, 194. Seyferth, D.; Marmor, R. S. Tetrahedron Lett. 1970, 2493; Seyferth, D.; Marmor, R. S.; Hilbert, P. J. J Org. Chem. 1971, 36, 1379.
62. Regitz, M.; Anschütz, W. Liebigs Ann. Chem. 1969, 730, 194. Seyferth, D.; Marmor, R. S. Tetrahedron Lett. 1970, 2493; Seyferth, D.; Marmor, R. S.; Hilbert, P. J. J Org. Chem. 1971, 36, 1379.
63. Regitz, M.; Anschütz, W. Liebigs Ann. Chem. 1969, 730, 194. Seyferth, D.; Marmor, R. S. Tetrahedron Lett. 1970, 2493; Seyferth, D.; Marmor, R. S.; Hilbert, P. J. J Org. Chem. 1971, 36, 1379.
64. Ohira, S. Synth. Comm. 1989, 19, 561 (using a reagent by Grieco, P. A.; Pogonowski, C. S. J. Am. Chem. Soc. 1973, 95, 3071).
65. Ohira, S. Synth. Comm. 1989, 19, 561 (using a reagent by Grieco, P. A.; Pogonowski, C. S. J. Am. Chem. Soc. 1973, 95, 3071).
66. Müller, S.; Liephold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521.
67. Miwa, K.; Aoyama, T.; Shioiri, T. Synlett 1994, 107.
68. Suffert, J. J. Org. Chem. 1989, 54, 509.
69. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.