Asymmetric synthesis of (-)-6-epi-centrolobine

Synthesis

Volumn , Issue 18, 2008, Pages 2939-2942

  Reddy, Chada Raji ^a   Madhavi, Pasupulety Phani ^a   Chandrasekhar, Srivari ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

C glycosidation; Centrolobine; Dehydroxylation; tri O acetyl D glucal; Wittig reaction

Indexed keywords

C-GLYCOSIDATION; CENTROLOBINE; DEHYDROXYLATION; TRI-O-ACETYL-D-GLUCAL; WITTIG REACTION;

CHEMICAL REACTIONS;

6 EPI CENTROLOBINE; ANTILEISHMANIAL AGENT; GLUCONATE CALCIUM; TRI O ACETYL DEXTRO GLUCAL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ACTIVITY; DRUG HYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSIDATION; INFRARED RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; WITTIG REACTION;

EID: 53249090528     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067218     Document Type: Article

References (22)

1. (a) de Albuquerque, I. L.; Galeffi, C.; Casinovi, C. G.; Marini-Bettolo, G. B. Gazz. Chim. Ital. 1964, 94, 287.
2. (b) Galeffi, C.; Giulio Casinovi, C.; Marini-Bettolo, G. B. Gazz. Chim. Ital. 1965, 95, 95.
3. (c) Craveiro, A. A.; Prado, A. d. C.; Gottlieb, O. R.; Welerson de Albuquerque, P. C. Phytochemistry 1970, 9, 1869.
4. Araujo, C. A. C.; Alefrio, L. V.; Leon, L. L. Phytochemistry 1998, 49, 751.
5. Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723.
6. (a) Marumoto, S.; Jaber, J. J.; Vitale, J. P.; Rychnovsky, S. D. Org. Lett. 2002, 4, 3919.
7. (b) Carreno, M. C.; Mazery, R. D.; Urbano, A.; Colobert, F.; Solladie, G. J. Org. Chem. 2003, 68, 7779.
8. (c) Evans, P. A.; Cui, J.; Gharpure, S. J. Org. Lett. 2003, 5, 3883.
9. (d) Lee, E.; Kim, H. J.; Jang, W. S. Bull. Korean Chem. Soc. 2004, 25, 1609.
10. (e) Boulad, L.; BouzzBouz, S.; Cossy, J.; Franck, X.; Figadère, B. Tetrahedron Lett. 2004, 45, 6603.
11. (f) Clarke, P. A.; Martin, W. H. C. Tetrahedron Lett. 2004, 45, 9061.
12. (g) Chan, K. P.; Loh, T. P. Org. Lett. 2005, 61, 4491.
13. (h) Clarke, P. A.; Martin, W. H. C. Tetrahedron 2005, 61, 5433.
14. (i) Jennings, M. P.; Clemens, R. T. Tetrahedron Lett. 2005, 46, 2021.
15. (j) Bohrsch, V.; Blechert, S. Chem. Commun. 2006, 1968.
16. (k) Lee, C. H. A.; Loh, T. P. Tetrahedron Lett. 2006, 47, 1641.
17. (l) Prasad, K. R.; Anbarasan, P. Tetrahedron 2007, 63, 1089.
18. (m) Washio, T.; Yamaguchi, R.; Abe, T.; Nambu, H.; Anada, M.; Hashimolo, S. Tetrahedron 2007, 63, 12037.
19. (n) Dziedzic, M.; Furman, B. Tetrahedron Lett. 2008, 49, 678.
20. Chandrasekhar, S.; Prakash, S. J.; Shyamsunder, T. Tetrahedron Lett. 2005, 46, 6651.
21. Ramnauth, J.; Poulin, O.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2013.
22. 4-Benzyloxybenzyl triphenylphosphonium bromide was prepared in two steps from commercially available p-benzyloxybenzyl alcohol using a known protocol, see ref. 4b.