On the diastereoselectivity of intramolecular Pd-catalyzed TMM cycloadditions. An asymmetric synthesis of the perhydroazulene (-)-isoclavukerin A

Journal of the American Chemical Society

Volumn 118, Issue 42, 1996, Pages 10094-10105

  Trost, Barry M ^a   Higuchi, Robert I ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZULENE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029906547     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961561m     Document Type: Article

References (70)

1. Bertz, S. H. J. Am. Chem. Soc. 1982, 104, 5801. Bertz, S. H.; Sommer, T. J. Org. Synth. Theory Appl. 1993, 2, 67. Wender, P. A.; Miller, B. L. Org. Synth. Theory Appl. 1993, 2, 27.
2. Bertz, S. H. J. Am. Chem. Soc. 1982, 104, 5801. Bertz, S. H.; Sommer, T. J. Org. Synth. Theory Appl. 1993, 2, 67. Wender, P. A.; Miller, B. L. Org. Synth. Theory Appl. 1993, 2, 27.
3. Bertz, S. H. J. Am. Chem. Soc. 1982, 104, 5801. Bertz, S. H.; Sommer, T. J. Org. Synth. Theory Appl. 1993, 2, 67. Wender, P. A.; Miller, B. L. Org. Synth. Theory Appl. 1993, 2, 27.
4. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 271-273.
5. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 271-273.
6. For some recent work, see: Trost, B. M.; Parquette, J. R.; Nübling, C. Tetrahedron Lett. 1995, 36, 2917. Trost, B. M.; Parquette, J. R.; Marquart, A. L. J. Am. Chem. Soc. 1995, 117, 3284. Trost, B. M.; Parquette, J. R. J. Org. Chem. 1994, 59, 7568.
7. For some recent work, see: Trost, B. M.; Parquette, J. R.; Nübling, C. Tetrahedron Lett. 1995, 36, 2917. Trost, B. M.; Parquette, J. R.; Marquart, A. L. J. Am. Chem. Soc. 1995, 117, 3284. Trost, B. M.; Parquette, J. R. J. Org. Chem. 1994, 59, 7568.
8. For some recent work, see: Trost, B. M.; Parquette, J. R.; Nübling, C. Tetrahedron Lett. 1995, 36, 2917. Trost, B. M.; Parquette, J. R.; Marquart, A. L. J. Am. Chem. Soc. 1995, 117, 3284. Trost, B. M.; Parquette, J. R. J. Org. Chem. 1994, 59, 7568.
9. For related cycloadditions, see: Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. Ohta, T.; Takaya, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds. Pergamon: Oxford, 1991; Vol. 5, pp 1185-1205 and also ref 2.
10. For related cycloadditions, see: Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. Ohta, T.; Takaya, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds. Pergamon: Oxford, 1991; Vol. 5, pp 1185-1205 and also ref 2.
11. Trost, B. M.; Grese, T. A.; Chan, D. M. T. J. Am. Chem. Soc. 1991, 113, 7350. Trost, B. M.; Grese, T. A. J. Am. Chem. Soc. 1991, 113, 7363. Trost, B. M.; Grese, T. A. J. Org. Chem. 1992, 57, 686.
12. Trost, B. M.; Grese, T. A.; Chan, D. M. T. J. Am. Chem. Soc. 1991, 113, 7350. Trost, B. M.; Grese, T. A. J. Am. Chem. Soc. 1991, 113, 7363. Trost, B. M.; Grese, T. A. J. Org. Chem. 1992, 57, 686.
13. Trost, B. M.; Grese, T. A.; Chan, D. M. T. J. Am. Chem. Soc. 1991, 113, 7350. Trost, B. M.; Grese, T. A. J. Am. Chem. Soc. 1991, 113, 7363. Trost, B. M.; Grese, T. A. J. Org. Chem. 1992, 57, 686.
14. Jenniskens, L. H. D.; Wijnberg, J. P. B. A.; De Groot, A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1994; Vol. 14, p 355. Fraga, B. M. Nat. Prod. Rep. 1992, 9, 217. Ho, T. L. Carbocyclic Construction in Terpene Synthesis; VCH Publishers: New York, 1988. Rigby, J. H. In Studies in Natural Products Chemistry; Attaur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, pp 545-576. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C; Plavac, F.; White, C. T. In Total Synthesis of Natural Products; Ap Simon, J., Ed.; Wiley: New York, 1982; Vol. 5, pp. 333-384.
15. Jenniskens, L. H. D.; Wijnberg, J. P. B. A.; De Groot, A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1994; Vol. 14, p 355. Fraga, B. M. Nat. Prod. Rep. 1992, 9, 217. Ho, T. L. Carbocyclic Construction in Terpene Synthesis; VCH Publishers: New York, 1988. Rigby, J. H. In Studies in Natural Products Chemistry; Attaur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, pp 545-576. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C; Plavac, F.; White, C. T. In Total Synthesis of Natural Products; Ap Simon, J., Ed.; Wiley: New York, 1982; Vol. 5, pp. 333-384.
16. Jenniskens, L. H. D.; Wijnberg, J. P. B. A.; De Groot, A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1994; Vol. 14, p 355. Fraga, B. M. Nat. Prod. Rep. 1992, 9, 217. Ho, T. L. Carbocyclic Construction in Terpene Synthesis; VCH Publishers: New York, 1988. Rigby, J. H. In Studies in Natural Products Chemistry; Attaur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, pp 545-576. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C; Plavac, F.; White, C. T. In Total Synthesis of Natural Products; Ap Simon, J., Ed.; Wiley: New York, 1982; Vol. 5, pp. 333-384.
17. Jenniskens, L. H. D.; Wijnberg, J. P. B. A.; De Groot, A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1994; Vol. 14, p 355. Fraga, B. M. Nat. Prod. Rep. 1992, 9, 217. Ho, T. L. Carbocyclic Construction in Terpene Synthesis; VCH Publishers: New York, 1988. Rigby, J. H. In Studies in Natural Products Chemistry; Attaur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, pp 545-576. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C; Plavac, F.; White, C. T. In Total Synthesis of Natural Products; Ap Simon, J., Ed.; Wiley: New York, 1982; Vol. 5, pp. 333-384.
18. Jenniskens, L. H. D.; Wijnberg, J. P. B. A.; De Groot, A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1994; Vol. 14, p 355. Fraga, B. M. Nat. Prod. Rep. 1992, 9, 217. Ho, T. L. Carbocyclic Construction in Terpene Synthesis; VCH Publishers: New York, 1988. Rigby, J. H. In Studies in Natural Products Chemistry; Attaur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, pp 545-576. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C; Plavac, F.; White, C. T. In Total Synthesis of Natural Products; Ap Simon, J., Ed.; Wiley: New York, 1982; Vol. 5, pp. 333-384.
19. For a recent example, see: Majetich, G.; Song, J. S.; Leigh, A. J.; Condon, S. M. J. Org. Chem. 1993, 58, 1030.
20. For a recent example, see: Takeuchi, N.; Fujita, T.; Goto, K.; Morisaki, N.; Osone, N.; Tobinaga, S. Chem. Pharm. Bull. 1993, 41, 923.
21. Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 5066. Harvey, D. F.; Brown, M. F. J. Org. Chem. 1992, 57, 5559. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523.
22. Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 5066. Harvey, D. F.; Brown, M. F. J. Org. Chem. 1992, 57, 5559. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523.
23. Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 5066. Harvey, D. F.; Brown, M. F. J. Org. Chem. 1992, 57, 5559. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523.
24. Cantrell, W. R., Jr.; Davies, H. M. L. J. Org. Chem. 1991, 56, 723. Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. For a review, see: Davies, H. M. L. Tetrahedron 1993,49, 5203. Also, see: Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919.
25. Cantrell, W. R., Jr.; Davies, H. M. L. J. Org. Chem. 1991, 56, 723. Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. For a review, see: Davies, H. M. L. Tetrahedron 1993,49, 5203. Also, see: Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919.
26. Cantrell, W. R., Jr.; Davies, H. M. L. J. Org. Chem. 1991, 56, 723. Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. For a review, see: Davies, H. M. L. Tetrahedron 1993,49, 5203. Also, see: Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919.
27. Cantrell, W. R., Jr.; Davies, H. M. L. J. Org. Chem. 1991, 56, 723. Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. For a review, see: Davies, H. M. L. Tetrahedron 1993,49, 5203. Also, see: Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919.
28. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720.
29. Kobayashi, M.; Son, B. W.; Kyogoku, Y.; Kitagawa, I. Chem. Pharm. Bull. 1984, 32, 1667. Kobayashi, M.; Son, B. W.; Kido, M.; Kyogohu, Y.; Kitagawa, I. Chem. Pharm. Bull. 1983, 31, 6.
30. Kobayashi, M.; Son, B. W.; Kyogoku, Y.; Kitagawa, I. Chem. Pharm. Bull. 1984, 32, 1667. Kobayashi, M.; Son, B. W.; Kido, M.; Kyogohu, Y.; Kitagawa, I. Chem. Pharm. Bull. 1983, 31, 6.
31. Kusumi, T.; Hamada, T.; Hara, M.; Ishitsuka, M. O.; Ginda, H.; Kakisawa, H. Tetrahedron Lett. 1992, 33, 2019.
32. Andersen, N. H.; Uh, H.-S. Tetrahedron Lett. 1973, 23, 2079. Marshall, J. A.; Greene, A. E. J. Org. Chem. 1972, 37, 982.
33. Andersen, N. H.; Uh, H.-S. Tetrahedron Lett. 1973, 23, 2079. Marshall, J. A.; Greene, A. E. J. Org. Chem. 1972, 37, 982.
34. Yoshikawa, M.; Yamaguchi, S.; Matsuda, H.; Kohda, Y.; Ishikawa, H.; Tanaka, N.; Yamahara, J.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 1813.
35. Rao, K. V.; Davis, T. L. Planta Med. 1982, 44, 249. For a synthesis, see: Saha, M.; Bagby, B.; Nicholas, K. M. Tetrahedron Lett. 1986, 27, 915.
36. Rao, K. V.; Davis, T. L. Planta Med. 1982, 44, 249. For a synthesis, see: Saha, M.; Bagby, B.; Nicholas, K. M. Tetrahedron Lett. 1986, 27, 915.
37. Shimizu, I.; Ishikawa, T. Tetrahedron Lett. 1994, 35, 1905.
38. Asaoka, M.; Kosaka, T.; Itahana, H.; Takei, H. Chem. Lett. 1991, 1295.
39. Honda, T.; Ishige, H.; Nagase, H. J. Chem. Soc., Perkin Trans. 1 1994, 3305.
40. Kim, K. S.; Pak, C. S. J. Org. Chem. 1991, 56, 6829.
41. Trost, B. M.; Nanninga, T. N.; Satoh, T. J. Am. Chem. Soc. 1985, 107, 721.
42. Jacobsen, R. M.; Lahm, G. P.; Clader, J. W. J. Org. Chem. 1980, 45, 395.
43. Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. J. Org. Chem. 1984, 49, 3938.
44. Walkup, R. D.; Boatman, P. D., Jr.; Kane, R. R.; Cunningham, R. T. Tetrahedron Lett. 1991, 32, 3937.
45. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
46. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399.
47. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.
48. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
49. Shahak, L.; Almog, J. Synthesis 1970, 145.
50. Tietze, L. F.; Beifuss, U. Annalen 1988, 321.
51. Lehnert, W. Tetrahedron 1973, 29, 635.
52. Trost, B. M.; Nanninga, T. N. J. Am. Chem. Soc. 1985, 107, 1293. Trost, B. M.; Renaut, P. J. Am. Chem. Soc. 1982, 104, 6668.
53. Trost, B. M.; Nanninga, T. N. J. Am. Chem. Soc. 1985, 107, 1293. Trost, B. M.; Renaut, P. J. Am. Chem. Soc. 1982, 104, 6668.
54. Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902. Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408.
55. Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902. Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408.
56. Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454.
57. Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477.
58. Posner, G. H.; Babiak, K. A.; Loomis, G. L.; Frazee, W. J.; Mittal, R. D.; Karle, I. L. J. Am. Chem. Soc. 1980, 102, 7498.
59. Burgess, E. M.; Penton, H. R., Jr.; Taylor, E. A. J. Org. Chem. 1973, 38, 26.
60. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
61. Comins, D. L.; Dehghani, A. Tetrahedron Leu. 1992, 33, 6299.
62. Shapiro, R. H. Org. React. 1976, 23, 406.
63. Chamberlin, A. R.; Bloom, S. H. Tetrahedron Lett. 1986, 27, 551 and earlier references cited therein. Baba, T.; Avasthi, K.; Suzuki, A. Bull. Chem. Soc. Jpn. 1983, 56, 1571.
64. Chamberlin, A. R.; Bloom, S. H. Tetrahedron Lett. 1986, 27, 551 and earlier references cited therein. Baba, T.; Avasthi, K.; Suzuki, A. Bull. Chem. Soc. Jpn. 1983, 56, 1571.
65. Shapiro, R. H.; Heath, M. J. J. Am. Chem. Soc. 1967, 89, 5736.
66. Caglioti, L.; Grasselli, P.; Selva, A. Gazz. Chim. Ital. 1964, 94, 537.
67. For an example, see: Trost, B. M.; Ohmori, M.; Boyd, S. A.; Okawara, H.; Brickner, S. J. J. Am. Chem. Soc. 1989, 111, 8281.
68. Bernasconi, S.; Comini, A.; Corbella, A.; Gariboldi, P.; Sisti, M. Synthesis 1980, 385.
69. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
70. Trost, B. M.; Miller, M. L. J. Am. Chem. Soc. 1988, 110, 3687.