Asymmetric total synthesis of (-)-alkaloid 223A and its 6-epimer

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4400-4405

  Pu, Xiaotao ^a   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

MICHAEL ADDITION;

ESTERS; HYDROGENATION; SYNTHESIS (CHEMICAL);

ALCOHOLS;

3 AMINO 2 ETHYLHEXANOL; ALKALOID; AMINOALCOHOL; ENAMINE; ESTER; GAMMA AMINO ALCOHOL DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM N BENZYL ALPHA METHYLBENZYLAMIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL MODIFICATION; CYCLIZATION; ENANTIOMER; EPIMER; HYDROGENATION; MOLECULAR DYNAMICS; STEREOCHEMISTRY;

ALKALOIDS; ANIMALS; ANURA; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; INDOLIZINES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM;

EID: 0037764781     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0341261     Document Type: Article

References (22)

1. (a) Garraffo, H. M.; Jain, P.; Spande, T. F.; Daly, J. W. J. Nat. Prod. 1997, 60, 2-5.
2. (b) Daly, J. W.; Garraffo, H. M.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press: New York, 1999; Vol. 13, pp 1-161.
3. (c) Daly, J. W. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 9-13.
4. (a) Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892.
5. (b) Michael, J. P. Nat. Prod. Rep. 1993, 51-72.
6. (c) Michael, J. P. Nat. Prod. Rep. 1994, 17-39.
7. Toyooka, N.; Fukutome, A.; Nemoto, H.; Daly, J. W.; Spande, T. F.; Garraffo, H. M.; Kaneko, T. Org. Lett. 2002, 4, 1715-1717.
8. (a) Ma, D.; Zhu, W. Org. Lett. 2001, 3, 3927-3929.
9. (b) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189-2191.
10. (c) Wang, Y.; Ma, D. Tetrahedron: Asymmetry 2001, 12, 725-729.
11. (d) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009-6016.
12. (e) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503-2505.
13. (f) Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947-1950.
14. (g) Ma, D.; Sun, H. Tetrahedron Lett. 1999, 40, 3609-3612.
15. (h) Ma, D.; Zhang, J. Tetrahedron Lett. 1998, 39, 9067-9068.
16. Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1991, 2, 183-186.
17. Seebach, D.; Estermann, H. Tetrahedron Lett. 1987, 28, 3103-3106.
18. Kirchanov, A. A.; Zanina, A. S.; Kotlyare-Vskii, L. L. Zh. Org. Khim. 1984, 21, 1406-1408.
19. Nicolaou, K. C.; Jung, J.; Yoon, W. H.; Fong, K. C.; Choi, H. S.; He, Y.; Zhong, Y.; Baron, D. S. J. Am. Chem. Soc. 2002, 124, 2183-2189.
20. Davies, S. G.; Ichihara, O.; Walters, I. S. J. Chem. Soc., Perkin Trans. 1 1994, 1141-1147.
21. (a) Stevens, R. V. Acc. Chem. Res. 1984, 17, 289-296.
22. (b) Deslongchamps, P. Stereoelectronic effects in organic chemistry; Pergamon Press: Oxford, UK, 1983.