Diastereoselective total synthesis of (-)-solavetivone via a copper-catalyzed conjugate addition of Me3Al to a cyclohexa-2,5-dienone intermediate

Tetrahedron

Volumn 53, Issue 2, 1997, Pages 603-616

  Takemoto, Yoshiji ^a   Kuraoka, Satoru ^a   Ohra, Taiichi ^a   Yonetoku, Yasuhiro ^a   Iwata, Chuzo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHYTOALEXIN; SESQUITERPENE; SOLAVETIVONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CIRCULAR DICHROISM; DRUG SYNTHESIS; ENANTIOMER; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031012572     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01006-X     Document Type: Article

References (43)

1. (a) Daniel, M.; Purkayastha, R. P. Handbook of phytoalexin metabolism and action, Marcel Dekker, Inc., New York, 1995;
2. (b) Afzal, M.; Al-Oriquat, G. Heterocydes, 1986, 24, 2943-2961;
3. (c) Murai, A. Yuki Gousei Kagaku Kyokaishi, 1981, 39, 893-908;
4. (d) Marshall, J. A.; Brady, S. F.; Anderson, N. H. Fortschr. Chem. Org. Naturst., 1974, 31, 283-376.
5. (a) Coxon, D. T.; Price, K. R.; Howard, B.; Osman, S. F.; Kalan, E. B.; Zacharius, R. M. Tetrahedron Lett., 1974, 2291-2294;
6. (b) T. Fujimori, R. Kasuga, H. Kaneko and M. Noguchi, Phytochemistry, 1977, 16, 392.
7. (a) Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett., 1994, 35, 2849-2852;
8. (b) Posner, G. H.; Shulman-Roskes, E. M. Tetrahedron, 1992, 48, 4677-4686;
9. (c) J. -E. Nystrom, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695-4698.
10. (a) Iwata, C.; Fusaka, T.; Fujiwara, T.; Tomita, K.; Yamada, M. J. Chem. Soc., Chem. Commun., 1981, 463-465; Iwata, C.; Yamada, M.; Fusaka, T.; Miyashita, K.; Nakamura, A.; Tanaka, T.; Fujiwara, T.; Tomita, K. Chem. Pharm. Bull., 1987, 35, 544-552;
11. (a) Iwata, C.; Fusaka, T.; Fujiwara, T.; Tomita, K.; Yamada, M. J. Chem. Soc., Chem. Commun., 1981, 463-465; Iwata, C.; Yamada, M.; Fusaka, T.; Miyashita, K.; Nakamura, A.; Tanaka, T.; Fujiwara, T.; Tomita, K. Chem. Pharm. Bull., 1987, 35, 544-552;
12. (b) Murai, A.; Sato, S.; Masamune, T. J. Chem. Soc., Chem. Commun., 1981, 904-905; Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn., 1984, 57, 2276-2281 and 2282-2285;
13. (b) Murai, A.; Sato, S.; Masamune, T. J. Chem. Soc., Chem. Commun., 1981, 904-905; Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn., 1984, 57, 2276-2281 and 2282-2285;
14. (c) Torii, S.; Uneyama, K.; Okamoto, K. Bull. Chem. Soc. Jpn., 1978, 51, 3590-3594;
15. (d) Yamada, K.; Goto, S.; Nagase, H.; Christensen, A. T. J. Chem. Soc., Chem. Commun., 1977, 554-555.
16. Hwu, J. R.; Wetzel, J. M. J. Org. Chem., 1992, 57, 922-928.
17. (a) Imanishi, T.; Ohra, T.; Sugiyama, K.; Ueda, Y.; Takemoto, Y.; Iwata, C. J. Chem. Soc., Chem. Commun., 1992, 269-270; Takemoto, Y.; Ohra, T.; Sugiyama, K.; Imanishi, T.; Iwata, C. Chem. Pharm. Bull., 1995, 43, 571-577.
18. (a) Imanishi, T.; Ohra, T.; Sugiyama, K.; Ueda, Y.; Takemoto, Y.; Iwata, C. J. Chem. Soc., Chem. Commun., 1992, 269-270; Takemoto, Y.; Ohra, T.; Sugiyama, K.; Imanishi, T.; Iwata, C. Chem. Pharm. Bull., 1995, 43, 571-577.
19. (b) Takemoto, Y.; Ohra, T.; Yonetoku, Y.; Nishimine, K.; Iwata, C. J. Chem. Soc., Chem. Commun., 1994, 81-82; Takemoto, Y.; Ohra, T.; Yonetoku, Y.; Iwata, C. Chem. Pharm. Bull., 1995, 43, 1859-1865.
20. (b) Takemoto, Y.; Ohra, T.; Yonetoku, Y.; Nishimine, K.; Iwata, C. J. Chem. Soc., Chem. Commun., 1994, 81-82; Takemoto, Y.; Ohra, T.; Yonetoku, Y.; Iwata, C. Chem. Pharm. Bull., 1995, 43, 1859-1865.
21. Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Tetrahedron, 1993, 49, 5483-5493; Mandai, T.; Suzuki, S.; Murakami, T.; Fujita, M.; Kawada, M.; Tsuji, J. Tetrahedron Lett., 1992, 33, 2987-2991.
22. Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Tetrahedron, 1993, 49, 5483-5493; Mandai, T.; Suzuki, S.; Murakami, T.; Fujita, M.; Kawada, M.; Tsuji, J. Tetrahedron Lett., 1992, 33, 2987-2991.
23. (a) Takemoto, Y.; Kuraoka, S.; Hamaue, N.; Iwata, C. Tetrahedron ; Asymmetry, 1996, 7, 993-996.;
24. (b) Takemoto, Y.; Kuraoka, S.; Hamaue, N.; Iwata, C. Tetrahedron, in submitted.
25. 3Al to a cyclohexa-2,5-dienone intermediate has been reported: Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. J. Chem. Soc., Chem. Commun., 1996, 1655-1656.
26. Isler, O.; Gutmann, H.; Montavon, M.; Ruegg, R.; Ryser, G.; Zeller, P. Helv. Chim. Acta, 1957, 40, 1242-1249.
27. (a) Larock, R. C.; Stinn, D. E; Kuo, M. Y. Tetrahedron Lett., 1990, 31, 17-20;
28. (b) Kang, S.-K.; Jung, K.-Y.; Park, C-H.; Namkoong, E.-Y.; and Kim, T.-H. Tetrahedron Lett., 1995, 36, 6287-6290;
29. (c) Jeffery, T.; Galland, J.-C. Tetrahedron Lett., 1994, 35, 4103-4106.
30. Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1, 1994, 2065-2072; Grennberg, H.; Gogoll, A.; Backväll, J. -E. J. Org. Chem., 1991, 50, 5808-5811; Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett., 1995, 36, 8035-8038.
31. Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1, 1994, 2065-2072; Grennberg, H.; Gogoll, A.; Backväll, J. -E. J. Org. Chem., 1991, 50, 5808-5811; Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett., 1995, 36, 8035-8038.
32. Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1, 1994, 2065-2072; Grennberg, H.; Gogoll, A.; Backväll, J. -E. J. Org. Chem., 1991, 50, 5808-5811; Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett., 1995, 36, 8035-8038.
33. Bueno, A. B.; Carreno, M.; Ruano, J. L. G. Tetrahedron Lett., 1993, 34, 5007-5010; Durst, T.; Tin, K.-C.; De Reinach-Hirtbach, F.; Decesare, J. M.; Ryan, M. D. Can. J. Chem., 1979, 57, 258-266.
34. Bueno, A. B.; Carreno, M.; Ruano, J. L. G. Tetrahedron Lett., 1993, 34, 5007-5010; Durst, T.; Tin, K.-C.; De Reinach-Hirtbach, F.; Decesare, J. M.; Ryan, M. D. Can. J. Chem., 1979, 57, 258-266.
35. Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc., 1976, 98, 4887-4902.
36. Bozzato, G.; Bachmann, J.-P.; Pesaro, M. J. Chem. Soc., Chem. Commun., 1974, 1005-1006.
37. McCurry, Jr., P. M.; Singh, R. K.; Link, S. Tetrahedron Lett., 1973, 1155-1158.
38. (a) Dines, M. B. J. Chem. Soc., Chem. Commun., 1973, 12-13.
39. (b) Salomon, R. G.; Kochi, J. K. J. Am. Chem. Soc., 1973, 95, 3300-3310.
40. Kirk, D. N. Tetrahedron, 1996, 42, 777-818; Burnett, R. D.; Kirk, D. N. J. Chem. Soc., Perkin Trans. 1, 1981, 1460-1468.
41. Kirk, D. N. Tetrahedron, 1996, 42, 777-818; Burnett, R. D.; Kirk, D. N. J. Chem. Soc., Perkin Trans. 1, 1981, 1460-1468.
42. Scherdrick, G. M. Acta Crystallogr., Sect. A, 1990, 46, 467-473.
43. SHELXL-93; Scherdrick, G. M. SHELXL-93 program for crystal structure refinement, University of Göttingen, Germany, 1993.