Radical cyclization of α-allenic ketone: A new approach to the synthesis of (±)-α-chamigrene

Tetrahedron

Volumn 52, Issue 41, 1996, Pages 13181-13188

  Chen, Yao Jung ^a   Wang, Chi Ying ^a   Lin, Wen Yuan ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CHAMIGRENE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030272517     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00785-5     Document Type: Article

References (30)

1. 1. (a) Curran, D. P. Synthesis 1988, 417 and 489.
2. (b) Ramaiah, M. Tetrahedron 1987, 43, 3541.
3. (c) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986.
4. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
5. 2. Giese, B. Angew. Chem. Int. Ed. Engl. 1983, 22, 753.
6. 3. (a) Burnett, D. A.; Choi, J. K.; Hart, D. J.; Tsai, Y. M. J. Am. Chem. Soc. 1984, 106, 8201.
7. (b) Apparu, M.; Crandall, J. K. J. Org. Chem. 1984, 49, 2125.
8. (c) Crandall, J. K.; Mualla, M. Tetrahedron Lett. 1986, 27, 2243.
9. (d) Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1993, 115, 7926.
10. 4. (a) Crandall, J. K.; Ayers, T. A. Tetrahedron Lett. 1991, 32, 3659.
11. (b) Gillmann, T. Tetrahedron Lett. 1993, 34, 607.
12. (c) Pasto, D. J.; L'Hermine, G. J. Org. Chem. 1990, 55, 685.
13. 5. (a) Ito, S.; Endo, K.; Yoshida, T.; Ytatagui, M.; Kodama, M. J. Chem. Soc., Chem. Commun. 1967, 186.
14. (b) Ohata, Y.; Hirose, Y. Tetrahedron Lett. 1968, 9, 2483.
15. 6. (a) Tanaka, A.; Uda, H.; Yoshikoshi, A. J. Chem. Soc., Chem. Commun. 1967, 188.
16. (b) Kanno, S.; Kato, T.; Kitahara, Y. J. Chem. Soc., Chem. Commun. 1967, 1257.
17. (c) Kitagawa, Y.; Hashimoto, S.; Iemura, S.; Yamamoto, H.;Nozaki, H.J. Am. Chem. Soc. 1976, 98, 5030.
18. (d) Martin, J. D.; Perez, C.; Ravelo, J. L. J. Am. Chem. Soc. 1986, 108, 7801.
19. (e) Plamondon, J.; Canonne, P. Tetrahedron Lett., 1991, 32, 589.
20. (f) White, J. D.; Torii, S.; Nogami, J. Tetrahedron Lett., 1974, 15, 2879.
21. (g) Iwata, C.; Yamada, M.; Shinoo, Y. Chem. Pharm. Bull., 1979, 27, 274.
22. 7. (a) Chen, Y. J.; Lin, W. Y. Tetrahedron Lett. 1992, 33, 1749.
23. (b) Chen, Y. J.; Chen, C. M.; Lin, W. Y. Tetrahedron Lett. 1993, 34, 2961.
24. (c) Chen, Y. J.; Lin, W. Y. Tetrahedron 1993, 45, 10263.
25. 8. Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782.
26. 9. (a) Hatem, J.; Henriet-Bernard, C. ; Grimaldi, J. ; Maurin, R. Tetrahedron Lett. 1992, 33, 1057.
27. (b) Bernard-Henriet, C. D. ; Grimaldi, J. R. ; Hatem, J. M. Tetrahedron Lett. 1994, 35, 3699.
28. 10. Ono, N.; Miyake, H.; Kamimura, A.; Tsukui, N.; Kaji, A. Tetrahedron Lett. 1982, 23, 2957.
29. 11. Bergbreiter, D. E.; LaLonde, J. J. J. Org. Chem. 1987, 52, 1601.
30. 12. Orru, R. V. A.; Wijnberg, J. B. P. A.; Bouwman, C. T.; Groot, A. J. Org. Chem. 1994, 59, 374.