A cycloaddition approach to breynolide

Tetrahedron

Volumn 53, Issue 26, 1997, Pages 8997-9006

  Martin, Stephen F ^a   Anderson, Bruce G ^a   Daniel, Dilon ^a   Gaucher, Anne ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYBENZOIC ACID; BREYNOLIDE; GLUCOSE; RHAMNOSE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; HYPERCHOLESTEROLEMIA; PLANT; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

BETULACEAE;

EID: 0030743506     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00582-6     Document Type: Article

References (35)

1. (a) Sasaki, K.; Hirata, Y. Tetrahedron Lett. 1973, 27, 2439.
2. (b) Sasaki, K.; Hirata, Y. Acta Cryst. 1974, B30, 1347.
3. Koshima, H.; Hatori, M.; Ohkuma, H.; Sakai, F.; Imanishi, H.; Ohbayashi, M.; Karvaguchi, H. Chem. Pharm. Bull. 1976, 24, 169.
4. Trost, W. IRCS Med. Sci. 1986, 14, 905.
5. Sakai, F.; Ohkuma, H.; Koshiyama, H.; Naito, T.; Kawaguchi, H. Chem. Pharm. Bull. 1976, 24, 114.
6. (a) Ohkuma, H.; Tsuno, T.; Konishi, M.; Naito, T.; Kawaguchi, H. Chem. Pharm. Bull. 1991, 39, 942.
7. (b) Smith, A. B., III; Keenan, T. P.; Gallagher, R. T.; Furst, G. T.; Dormer, P. G. J. Org. Chem. 1992, 57, 5115.
8. Nishiyama, S.; Ikeda, Y.; Yoshida, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 105.
9. Williams, D. R.; Jass, P. A.; Allan Tse, H-L.; Gaston, R. D. J. Am. Chem. Soc. 1990, 112, 4552.
10. (a) Smith, A. B., III; Empfield, J. R.; Rivero, R. A.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 4037.
11. (b) Smith, A. B., III; Empfield, J. R.; Rivero, R. A.; Vaccaro, H. A.; Duan, J. J.-W.; Sulikowski, M. M. J. Am. Chem. Soc. 1992, 114, 9419.
12. Martin, S. F.; Daniel, D. Tetrahedron Lett. 1993, 34, 4281.
13. Linderman, R. J.; Cutshall, N. S.; Becicka, B. T. Tetrahedron Lett. 1994, 35, 6639.
14. Martin, S. F.; Dappen, M. S.; Dupré, B.; Murphy, C. J.; Colapret, J. A. J. Org. Chem. 1989, 54, 2209.
15. Martin, S. F.; Dupré, B. Tetrahedron Lett. 1983, 24, 1337.
16. (a) Grünanger, P.; Gandolfi, R.; De Micheli, C.; Bianchi, G.; Finzi, P. V.; Vajna de Pava, O. J. C. S. Perkin 1 1973, 1148.
17. (b) Muckensturm, B.; Riss, B.P. Tetrahedron Lett. 1986, 27, 4979.
18. Danishefsky, S.; Kitahara, T. J. Am. Chem. Soc. 1974, 96, 7807.
19. Lynch, V. M.; Daniel, D.; Martin, S. F.; Davis, B. E. Acta Cryst. 1991, C47, 1340.
20. Lynch, V. M.; Daniel, D.; Martin, S. F.; Davis, B. E. Acta Cryst. 1990, C46, 708.
21. (a) Koizuma, T.; Hiraiand, H.; Yoshii, E. J. Org. Chem. 1982,47, 4004.
22. (b) Maignan, C.; Raphael, R. Tetrahedron 1983, 39, 3245.
23. (c) Maignan, C.; Guessous, A.; Rouessac, F. Tetrahedron Lett. 1984, 25, 1727.
24. (d) Koizuma, T.; Hakamada, I.; Yoshii, E. Tetrahedron Lett. 1984, 25, 87.
25. (e) Khan, S.; Hehre W. Tetrahedron Lett. 1986, 27, 6041.
26. (f) DeLucchi, O.; Lucchini, V.; Marchiaro, C.; Valle, G; Modena, G. J. Org. Chem. 1986, 51, 1457.
27. (g) Ando, W., Hanyu, Y. Takata, T. J. Org. Chem. 1986, 57, 2122.
28. Kagan, H.; Samuel, O.; Zhao, S. Tetrahedron 1987, 43, 5135.
29. (a) Gardner, J. N.; Kaiser, S.; Krubiner, A.; Lucas, H. Can. J. Chem. 1973, 51, 1419.
30. (b) Kemp, D. S.; Buckler, D. R. J. Org. Chem. 1989, 54, 3647.
31. (a) Swem, D.; Huang, S-L.; Mancuso, A. J. J. Org. Chem. 1978, 43, 2480.
32. (b) For a review, see: Tidwell, T. T. Synthesis, 1990, 857.
33. Antonakis, K.; Egron, M.; Herscovici, J. J. Chem. Soc. Perkin Trans. I 1982, 1967.
34. Chasar, D.; Pratt, T. Synthesis 1976, 263.
35. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339.