New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction

Tetrahedron Letters

Volumn 41, Issue 31, 2000, Pages 5923-5926

  Tokuzaki, Kazuo ^a   Kanemitu, Yasuhiro ^a   Yoshimitsu, Takehiko ^a   Nagaoka, Hiroto ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Antitumor compounds; Michael reactions; Terpenes and terpenoids

Indexed keywords

CYCLOPENTENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; PANTOLACTONE; SESQUITERPENE DERIVATIVE;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034729922     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00974-6     Document Type: Article

References (23)

1. (a) Anchel, M., Hervey, A., Robbins, W. J. Proc. Natl. Acad. Sci. USA 1952, 38, 927-928.
2. (b) Shirahama, H.; Komatsu, T. Bull. Chem. Soc. Jpn. 1962, 35, 1047-1048.
3. (c) Nakanishi, K.; Tada, M.; Yamada, Y.; Ohashi, M.; Komatsu, N.; Terakawa, H. Nature 1963, 197, 292.
4. (d) Nakanishi, K.; Ohashi, M.; Tada, M.; Yamada, Y. Tetrahedron, 1965, 21, 1231-1246.
5. (f) McMorris, T. C.; Anchel, M. J. Am. Chem. Soc. 1963, 85, 831-832.
6. (g) Matsumoto, T.; Shirahama, H.; Ichihara, A.; Fukuoka, Y.; Takahashi, Y.; Mori, Y.; Watanabe, M. Tetrahedron 1965, 21, 2671-2676.
7. (a) McMorris, T. C.; Kelner, M. J.; Wang, W.; Estes, L. A.; Montoya, M. A.; Taelte, R. J. Org. Chem., 1992, 57, 6876-6883.
8. (b) Kelner, M. J.; McMorris, T. C.; Estes, L. A.; Montoya, M. A.; Wang, W.; Samson, K. M.; Taetle, R. Investigational New Drugs 1996, 14, 161-167.
9. (c) McMorris, T. C.; Yu, J.; Hu, Y. J. Org. Chem. 1997, 62, 3015-3018.
10. (a) Matsumoto, T.; Shirahama, H.; Ichihara, A.; Shin, H.; Kagawa, S.; Sakan, F.; Matsumoto, S.; Nishida, S. J. Am. Chem. Soc. 1968, 90, 3280-3281;
11. (b) Matsumoto, T.; Shirahama, H.; Ichihara, A.; Shin, H.; Kagawa, S.; Sakan, F.; Miyano, K. Tetrahedron Lett. 1971, 23, 2049-2052.
12. (c) Kinder Jr., F. R.; Bair, K. W. J. Org. Chem. 1994, 59, 6965-6967.
13. (d) Padwa, A.; Sandanayaka, V. P.; Curtis, E. A. J. Am. Chem. Soc. 1994, 116, 2667-2668.
14. (e) Padwa, A.; Curtis, E. A.; Sandanayaka, V. P. J. Org. Chem. 1997, 62, 1317-1325.
15. (a) Salaün, J.; Bennani, F.; Compain, J. C.; Fadel, A.; Ollivier, J. J. Org. Chem. 1980, 45, 4129-4135.
16. (b) Spitzner, D.; Swoboda, H. Tetrahedron Lett. 1986, 27, 1281-1284.
17. Miyaoka, H.; Sagawa, S.; Nagaoka, H.; Yamada, Y. Tetrahedron: Asymmetry 1995, 6, 587-594.
18. Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 274-278.
19. 3N, DMAP), 23 and 24, which were derived from 12, respectively. The relative configuration of 19 was determined by NOESY experiment.
20. Basavaiah, D.; Gowriswari, V. V. L. Tetrahedron Lett. 1986, 27, 2031-2032.
21. Attempts at mesylation and tosylation of the hydroxy group in 9 were unsuccessful.
22. 2, 0°C, 33%.
23. Fukuyama, T.; Vranesic, B.; Negri, D. P.; Kishi, Y. Tetrahedron Lett. 1978, 2741-2744.