Mercaptolysis of the E/F rings of steroidal sapogenins: A concise synthesis of Δ20(22)-furostene-26-thioethers

Chinese Journal of Chemistry

Volumn 21, Issue 7, 2003, Pages 784-788

  Tian, Wei Sheng ^a   Guan, Hui Ping ^b   Pan, Xin Fu ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Mercaptolysis; Steroidal sapogenin; Synthesis; 20(22) furostene 26 thioethers

Indexed keywords

EID: 33748083026     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20030210714     Document Type: Article

References (22)

1. (a) Redpath, J.; Zeelen, F. J. Chem. Soc. Rev. 1983, 25, 75.
2. (b) Pialak, D. M.; Wicha, J. Chem. Rev. 1978, 78, 199.
3. (a) Tian, W. S.; He, L. W.; Wang, C. In Advances in Steroid Chemistry; Ed.: Zhou W. S.; Zhuang, Z. P., Science Press, Beijing, 2001, p. 204 (in Chinese).
4. (b) Zhu, G. D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877.
5. (a) Jiang, B.; Huang, L. F.; Tian, W. S.; Zhou, W. S. In Studies in Natural Products Chemistry, Ed.: Attaur-Rahman, Elsevier, Amsterdam, 1997, p. 19, p. 245.
6. (b) Cutler, H. G.; Yokota, T.; Adam, G. Brassinosteroids Chemistry, Bioactivity and Applications, ACS Symposium Series 474, Washington DC, 1991.
7. Cao, M. X.; Jian, R. J. In Advances in Steroid Chemistry, Ed.: Zhou, W. S., Science Press, Beijing, 2001, p. 370 (in Chinese).
8. Tian, W. S.; Yang, Q. X. In Advances in Steroid Chemistry, Ed.: Zhou, W. S., Science Press, Beijing, 2001, p. 301 (in Chinese).
9. (b) Kim, S.; Sutton, S. C.; Guo, C.; Lacour, T. G.; Fuchs, P. L. J. Am. Chem. Soc. 1999, 121, 2056.
10. (a) Guo, C. X.; Fuchs, P. L. Tetrahedron Lett. 1998, 39, 1099.
11. (b) Deng, S. J.; Yu, B.; Lou, Y.; Hui, Y. Z. J. Org. Chem. 1999, 64, 202.
12. (c) Yu, W. S.; Jin, Z. D. J. Am. Chem. Soc. 2001, 123, 3367.
13. (d) Yu, W. S.; Jin, Z. D. J. Am. Chem. Soc. 2002, 124, 6576.
14. Djerassi, C.; Halpern, O.; Pettit, G. R.; Thomas, G. H. J. Org. Chem. 1959, 24, 1.
15. He, M. S. Master Dissertation, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 1998.
16. Fawl, W. H.; Failli, A.; Djerassi, C. J. Org. Chem. 1970, 35, 2571.
17. Schroepfer, G. J., Jr.; Kim, H. S.; Wilson, W. K.; Needleman, D. H.; Pinkerton, F. D.; Wilson, D. K.; Quiocho, F. A. J. Lipid Res. 1989, 30, 247.
18. Hermandez, R.; Tellado, J. J. M.; Prout, K.; Suarez, E. J. Chem. Soc., Chem. Commun. 1992, 275.
19. Tian, W. S.; Guan, H. P.; Pan, X. F. Chin. Chem. Lett. 1994, 5, 1013.
20. Wang, J. Q.; Tian, W. S. J. Chem. Soc., Perkin Trans. 1 1996, 2, 209.
21. Lowry, T. M.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3th ed., Harper & Row Publisher Inc., New York, 1987, p. 318.
22. Bovicelli, P.; Lupattelli, P.; Fracassi, D. Tetrahedron Lett. 1994, 35, 935.