Stereospecific, Enantiospecific Total Synthesis of the Sarpagine Indole Alkaloids (E)16-Epiaffinisine, (E)16-Epinormacusine B, and Dehydro-16-epiaffinisine

Organic Letters

Volumn 4, Issue 26, 2002, Pages 4681-4684

  Yu, Jianming ^a   Liao, Xuebin ^a   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(E)16 EPIAFFINISINE; (E)16 EPINORMACUSINE B; (E)16-EPIAFFINISINE; (E)16-EPINORMACUSINE B; ALKALOID; DEHYDRO 16 EPIAFFINISINE; DEHYDRO-16-EPIAFFINISINE; DRUG DERIVATIVE; INDOLE ALKALOID; INDOLE DERIVATIVE; N METHYLTRYPTOPHAN; TRYPTOPHAN;

ARTICLE; CHEMISTRY; MEDICINAL PLANT; STEREOISOMERISM; SYNTHESIS; TREE;

ALKALOIDS; INDOLE ALKALOIDS; INDOLES; PLANTS, MEDICINAL; STEREOISOMERISM; TREES; TRYPTOPHAN;

EID: 0038272218     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020209c     Document Type: Article

References (25)

1. Clivio, P.; Richard, B.; Deverre, J.-R.; Sevenet, T.; Zeches, M.; Le Men-Olivier, L. Phytochemistry 1991, 30, 3785.
2. Van Beek, T. A.; Verpoorte, R.; Baerheim Svendsen, A.; Leeuwenberg, A. J. M.; Bisset, N. G. J. Ethnopharm. 1984, 10, 1.
3. Haginiwa, J.; Sakai, S.; Kubo, A.; Hamamoto, T. Yakugaku Zasshi 1967, 87, 1484.
4. (a) Magnus, P.; Mugrage, B.; DeLuca, M.; Cain, G. A. J. Am. Chem. Soc. 1989, 111, 786.
5. (b) Magnus, P.; Mugrage, B.; DeLuca, M.; Cain, G. A. J. Am. Chem. Soc. 1990, 112, 5220.
6. Yu, P.; Wang, T.; Li, J.; Cook, J. M. J. Org. Chem. 2000, 65, 3173.
7. Liu, X.; Zhang, C.; Liao, X.; Cook, J. M. Tetrahedron Lett. 2002, 43, 7373.
8. Wang, T.; Cook, J. M. Org. Lett. 2000, 2, 2057.
9. Zhao, S.; Liao, X.; Cook, J. M. Org. Lett. 2002, 4, 687.
10. Liu, X. Ph.D. Thesis, University of Wisconsin-Milwaukee, 2002.
11. Brown, H. C.; Keblys, K. A. J. Am. Chem. Soc. 1964, 86, 1791.
12. Pinchon, T.-M.; Nuzillard, J.-M.; Richard, B.; Massiot, G.; Le Men-Olivier, L.; Sevenet, T. Photochemistry 1990, 29, 3341.
13. Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1977, 42, 1213.
14. Oikawa, Y.; Yoshioka, T.; Kunihiko, M.; Yonemitsu, O. Hetreocycles 1979, 12, 1457.
15. Campus, O.; DiPerro, M.; Cain, M.; Mantei, R.; Gawish, A.; Cook, J. M. Heterocycles 1980, 14, 975.
16. Cain, M.; Mantei, R.; Cook, J. M. J. Org. Chem. 1982, 47, 4933.
17. Wang, T.; Xu, Q.; Yu, P.; Liu, X.; Cook, J. M. Org. Lett. 2001, 3, 345.
18. Walker, D.; Hiebert, J. D. Chem. Rev. 1967, 67, 153.
19. Braude, E. A.; Jackman, L. M.; Linstead, R. P. J. Chem. Soc. 1954, 3548.
20. Jackman, L. M. Adv. Org. Chem. 1960, 2, 329.
21. Bergman, J.; Carlsson, R.; Misztal, S. Acta Chem. Scand. B 1976, 30, 853.
22. (a) Yu, P.; Wang, T.; Yu, F.; Cook, J. M. Tetrahedron Lett. 1997, 38, 6819.
23. (b) Wang, T.; Yu, P.; Li, J.; Cook, J. M. Tetrahedron Lett. 1998, 39, 8009.
24. (c) Li, J.; Wang, T.; Yu, P.; Peterson, A.; Weber, R.; Soerens, D.; Grubisha, D.; Bennett, D.; Cook, J. M. J. Am. Chem. Soc. 1999, 121, 6998.
25. (d) Yu, P.; Cook, J. M. J. Org. Chem. 1998, 63, 9160.