A novel, stereospecific total synthesis of (±)-Δ(9(12)-Capnellene from p-Cresol

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2911-2914

  Singh, Vishwakarma ^a   Prathap, S ^a   Porinchu, M ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DELTA9(12) CAPNELLENE; SESQUITERPENE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030905235     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00501-7     Document Type: Article

References (30)

1. (a) Mayer, C.; Marek, I.; Normant, J. F., Tetrahedron Lett., 1996, 37, 857-860,
2. (b) Clive, D. L. J.; Magnuson, S. R.; Manning, H. W.; Mayhew, D. L., J. Org. Chem., 1996, 61, 2095-2108,
3. (c) Enholm, E. J.; Jia, Z. J., J. Chem. Soc., Chem. Commun., 1996, 1567-1568.
4. (a) Clive, D. L. J.; Magnuson, S. R., Tetrahedron Lett., 1995, 36, 15-18,
5. (b) Inoue, T.; Hosomi, K.; Araki, M.; Nishide, K.; Node, M., Tetrahedron Asymmetry, 1995, 6, 31-34,
6. (c) Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A., Tetrahedron Lett., 1995, 36, 4651-4654.
7. (a) Pattenden, G.; Teague, S. J., J. Chem. Soc. Perkin Trans. I, 1988, 1077-1083,
8. (b) Paquette, L. A., Doherty, A. M. in Reactivity and Structure, Concepts in Organic Chemistry Vol 26 (Eds. Hafher, L.; Rees, C. W.; Trost, B. M.; Lehn, J. M.; Schleyer, P. v. R.; Zahradinik, R.), Springer-Verlag, New York, 1987 and references cited therein,
9. (c) Ley, S. V.; Murray, P. J.; Palmer, B. D, Tetrahedron, 1985, 41, 4765-4769,
10. (d) Wender, P. A.; Howbert, J. J., Tetrahedron Lett., 1983, 5325-5328.
11. (a) Ohshima, T.; Kagechika, K.; Adachi, M.; Sodeoka, M.; Shibasaki, M., J. Am. Chem. Soc., 1996, 118, 7108-7116,
12. (b) Tanaka, K.; Ogasawara, K., J. Chem. Soc., Chem. Commun., 1996, 1839-1840,
13. (c) Balme, G.; Bouyssi, D., Tetrahedron, 1994, 50, 403-414 and references cited therein.
14. (a) Ihara, M.; Suzuki, T.; Katogi, M.; Taniguchi, N.; Fukumoto, K., J. Chem. Soc., Chem. Commun., 1991, 646-647,
15. (b) Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N., J. Org. Chem., 1990, 55, 4504-4506,
16. (c) Stille, J. R.; Grubbs, R. H., J. Am. Chem. Soc., 1986, 108, 855-856,
17. (d) Curran, D. P.; Chen, M. H., Tetrahedron Lett., 1985, 26, 4991-4994,
18. (e) Mehta, G.; Reddy, D. S.; Murty, J., J. Chem. Soc., Chem. Commun., 1983, 824-825,
19. (f) Birch, A. M.; Pattenden, G., Tetrahedron Lett., 1982, 23, 991-994,
20. (g) Fujita, T; Ohtsuka, T.; Shirahama, H.; Matsumoto, T., Tetrahedron Lett., 1982, 23, 4091-4094,
21. (h) Oppolzer, W.; Batig, K., Tetrahedron Lett., 1982, 23, 4669-4672. For other syntheses of capnellene see reference 4c.
22. (a) Zimmerman, H. E.; Armesto, D., Chem. Rev., 1996, 96, 3065-3112,
23. (b) Eckersley, T. J.; Parker, S. D.; Rogers, N. A.. J., Tetrahedron, 1984, 40, 3749-3758,
24. (c) Horspool, W. M. (ed.) Synthetic Organic Photochemistry, Plenum, New York, 1984,
25. (d) Singh, V. K. ; Prathap, S., Synlett, 1994, 542-544.
26. Singh, V. K.; Deota, P. T., J. Chem. Res., 1989, 390-391.
27. Keinan, E.; Greenspoon, N. in Comprehensive Organic Synthesis Vol. 8 (Eds. Trost, B. M.; Fleming, I.), Pergamon Press, Oxford, 1991, pp. 523-578.
28. Wong, H. N. C.; Hon, M. Y.; Tse, C. W.; Yib, Y. C.; Taneko, T.; Hudlicky, T., Chem. Rev., 1989, 89, 165-198.
29. Little, R. D.; Carroll, G. L.; Petersen, J. L., J. Am. Chem. Soc., 1983, 105, 928-932.
30. +). These spectral features are in good agreement with those reported in the literature.4a