First synthesis of a bidesmosidic triterpene saponin by a highly efficient procedure [7]

Journal of the American Chemical Society

Volumn 121, Issue 51, 1999, Pages 12196-12197

  Yu, Biao ^a   Xie, Jianming ^a   Deng, Shaojiang ^a   Hui, Yongzheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

SAPONIN; TRITERPENE;

CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; GLYCOSYLATION; LETTER; SYNTHESIS;

EID: 0033616086     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9926818     Document Type: Letter

References (30)

1. (a) Rouhi, A. M. Chem. Eng. News 1995, 73 (Sept 11), 28-35.
2. (b) Hostettmann, K.; Marston, A. Saponins; Cambridge University Press: Cambridge, UK, 1995.
3. (c) Saponins Used in Traditional and Modern Medicine; Waller, G. R., Yamasaki, K., Eds.; Advances in Experimental Medicine and Biology 404; Plenum Press: New York, 1996.
4. For previous efforts on the total synthesis of saponins, see: (a) Randolph, J. T.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5693-5700. (b) Nishizawa, M.; Yamada, H. Synlett 1995, 785-793. (c) Deng, S.; Yu, B.; Hui, Y. Tetrahedron Lett. 1998, 39, 6511-6514. (d) Deng, S.; Yu, B.; Lou, Y.; Hui, Y. J. Org. Chem. 1999, 64, 202-208.
5. For previous efforts on the total synthesis of saponins, see: (a) Randolph, J. T.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5693- 5700. (b) Nishizawa, M.; Yamada, H. Synlett 1995, 785-793. (c) Deng, S.; Yu, B.; Hui, Y. Tetrahedron Lett. 1998, 39, 6511-6514. (d) Deng, S.; Yu, B.; Lou, Y.; Hui, Y. J. Org. Chem. 1999, 64, 202-208.
6. For previous efforts on the total synthesis of saponins, see: (a) Randolph, J. T.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5693- 5700. (b) Nishizawa, M.; Yamada, H. Synlett 1995, 785-793. (c) Deng, S.; Yu, B.; Hui, Y. Tetrahedron Lett. 1998, 39, 6511-6514. (d) Deng, S.; Yu, B.; Lou, Y.; Hui, Y. J. Org. Chem. 1999, 64, 202-208.
7. For previous efforts on the total synthesis of saponins, see: (a) Randolph, J. T.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5693- 5700. (b) Nishizawa, M.; Yamada, H. Synlett 1995, 785-793. (c) Deng, S.; Yu, B.; Hui, Y. Tetrahedron Lett. 1998, 39, 6511-6514. (d) Deng, S.; Yu, B.; Lou, Y.; Hui, Y. J. Org. Chem. 1999, 64, 202-208.
8. (a) Shao, C. J.; Kasai, R.; Xu, J. D.; Tanaka, O. Chem. Pharm. Bull. 1988, 36, 601-608.
9. (b) Reference 1b, pp 337-341.
10. (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155-173.
11. (b) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235.
12. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
13. (d) Boons, G.-J. Contemp. Org. Synth. 1996, 173-200.
14. For "one-pot glycosylation", see: (a) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581. (b) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919-7920. (c) Chenault, H. K.; Castro, A. Tetrahedron Lett. 1994, 35, 9145-9148. (d) Ley, S. V.; Priepke, H. W. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2292-2294. (e) Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753. (f) Yamada, H.; Kato, T.; Takahashi, T. Tetrahedron Lett. 1999, 40, 4581-4584.
15. For "one-pot glycosylation", see: (a) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581. (b) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919-7920. (c) Chenault, H. K.; Castro, A. Tetrahedron Lett. 1994, 35, 9145-9148. (d) Ley, S. V.; Priepke, H. W. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2292-2294. (e) Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753. (f) Yamada, H.; Kato, T.; Takahashi, T. Tetrahedron Lett. 1999, 40, 4581-4584.
16. For "one-pot glycosylation", see: (a) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581. (b) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919-7920. (c) Chenault, H. K.; Castro, A. Tetrahedron Lett. 1994, 35, 9145-9148. (d) Ley, S. V.; Priepke, H. W. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2292-2294. (e) Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753. (f) Yamada, H.; Kato, T.; Takahashi, T. Tetrahedron Lett. 1999, 40, 4581-4584.
17. For "one-pot glycosylation", see: (a) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581. (b) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919-7920. (c) Chenault, H. K.; Castro, A. Tetrahedron Lett. 1994, 35, 9145-9148. (d) Ley, S. V.; Priepke, H. W. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2292-2294. (e) Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753. (f) Yamada, H.; Kato, T.; Takahashi, T. Tetrahedron Lett. 1999, 40, 4581-4584.
18. For "one-pot glycosylation", see: (a) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581. (b) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919-7920. (c) Chenault, H. K.; Castro, A. Tetrahedron Lett. 1994, 35, 9145-9148. (d) Ley, S. V.; Priepke, H. W. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2292-2294. (e) Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753. (f) Yamada, H.; Kato, T.; Takahashi, T. Tetrahedron Lett. 1999, 40, 4581-4584.
19. For "one-pot glycosylation", see: (a) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581. (b) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919-7920. (c) Chenault, H. K.; Castro, A. Tetrahedron Lett. 1994, 35, 9145-9148. (d) Ley, S. V.; Priepke, H. W. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2292-2294. (e) Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753. (f) Yamada, H.; Kato, T.; Takahashi, T. Tetrahedron Lett. 1999, 40, 4581-4584.
20. For "two-directional glycosylation", see: (a) Zhu, T.; Boons, G.-J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1898-1900. (b) Zhu, T.; Boons, G.- J. Tetrahedron Lett. 1998, 39, 2187-2190. (c) Zhu, T.; Boons, G.-J. J. Chem. Soc., Perkin Trans. 1 1998, 857-861. (d) Boons, G.-J.; Bowers, S.; Coe, D. M. Tetrahedron Lett. 1997, 38, 3773-3776. (e) Boons, G.-J.; Zhu, T. Synlett 1997, 809-811.
21. For "two-directional glycosylation", see: (a) Zhu, T.; Boons, G.-J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1898-1900. (b) Zhu, T.; Boons, G.-J. Tetrahedron Lett. 1998, 39, 2187-2190. (c) Zhu, T.; Boons, G.-J. J. Chem. Soc., Perkin Trans. 1 1998, 857-861. (d) Boons, G.-J.; Bowers, S.; Coe, D. M. Tetrahedron Lett. 1997, 38, 3773-3776. (e) Boons, G.-J.; Zhu, T. Synlett 1997, 809-811.
22. For "two-directional glycosylation", see: (a) Zhu, T.; Boons, G.-J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1898-1900. (b) Zhu, T.; Boons, G.- J. Tetrahedron Lett. 1998, 39, 2187-2190. (c) Zhu, T.; Boons, G.-J. J. Chem. Soc., Perkin Trans. 1 1998, 857-861. (d) Boons, G.-J.; Bowers, S.; Coe, D. M. Tetrahedron Lett. 1997, 38, 3773-3776. (e) Boons, G.-J.; Zhu, T. Synlett 1997, 809-811.
23. For "two-directional glycosylation", see: (a) Zhu, T.; Boons, G.-J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1898-1900. (b) Zhu, T.; Boons, G.- J. Tetrahedron Lett. 1998, 39, 2187-2190. (c) Zhu, T.; Boons, G.-J. J. Chem. Soc., Perkin Trans. 1 1998, 857-861. (d) Boons, G.-J.; Bowers, S.; Coe, D. M. Tetrahedron Lett. 1997, 38, 3773-3776. (e) Boons, G.-J.; Zhu, T. Synlett 1997, 809-811.
24. For "two-directional glycosylation", see: (a) Zhu, T.; Boons, G.-J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1898-1900. (b) Zhu, T.; Boons, G.- J. Tetrahedron Lett. 1998, 39, 2187-2190. (c) Zhu, T.; Boons, G.-J. J. Chem. Soc., Perkin Trans. 1 1998, 857-861. (d) Boons, G.-J.; Bowers, S.; Coe, D. M. Tetrahedron Lett. 1997, 38, 3773-3776. (e) Boons, G.-J.; Zhu, T. Synlett 1997, 809-811.
25. Kitagawa, I.; Back, N. I.; Ohashi, K.; Sakagami, M.; Yoshikawa, M.; Shibuya, H. Chem. Pharm. Bull. 1989, 37, 1131-1133.
26. The present conditions used for glycosylation of a sapogenin have been found to be ideal, see: Deng, S.; Yu, B.; Xie, J.; Hui, Y. J. Org. Chem. 1999, 64, 7265-7266.
27. The ester glycosidic linkage at C-28 of a pentacyclic triterpene has been found to be rather resistant to basic hydrolysis. See ref 1b, pp 185, and references cited therein.
28. (a) Murata, S.; Noyori, R. Tetrahedron Lett. 1981, 22, 2107-2108.
29. (b) Berlin, K. D.; Gower, L. H.; White, J. W.; Gibbs, D. E.; Sturm, G. P. J. Org. Chem. 1962, 27, 3595-3597.
30. Zhu and Boons also employed two flasks in their sequential glycosylation, see ref be.