A simple and efficient synthesis of (±)-mesembrine

Tetrahedron Letters

Volumn 45, Issue 27, 2004, Pages 5263-5265

  Chavan, Subhash P ^a   Khobragade, Dushant A ^a   Pathak, Ashok B ^a   Kalkote, U R ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Alkaloids; Deprotection; Michael addition; Protection; Wittig reaction

Indexed keywords

ALKALOID; MESEMBRINE; SEROTONIN UPTAKE INHIBITOR; UNCLASSIFIED DRUG;

CONFERENCE PAPER; DRUG SYNTHESIS; MICHAEL ADDITION; QUANTUM YIELD;

EID: 2942548185     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.021     Document Type: Conference Paper

References (22)

1. Kulkarni M.G., Rasne R.M., Davawala S.I., Doke A.K. Tetrahedron Lett. 43:2002;2297-2298. and references cited therein
2. Taber D.F., Neubert T.D. J. Org. Chem. 66:2001;143-147. and references cited therein
3. Rigby J.H., Dong W. Org. Lett. 2:2000;1673-1675. and references cited therein
4. Gericke, N. P.; Van Wyk, B. E. World Patent 9,746,234, 1997; Chem. Abstr. 1998, 128, 80030
5. Posner G.H., Kogan T.P., Hulce M. Tetrahedron Lett. 25:1984;383-386
6. Pfau M., Revial G., Guingant A., d'Angelo J. J. Am. Chem. Soc. 107:1985;273-274
7. Koga K., Tomioka K., Cho Y.S., Sato F. J. Org. Chem. 53:1988;4094-4098
8. Fukumoto K., Ihara M., Takahashi M., Niitsuma H., Taniguchi N., Yasui K. J. Org. Chem. 54:1989;5413-5415
9. Lee E., Shin I.J., Kim T.S. J. Am. Chem. Soc. 112:1990;260-264
10. Overman L.E., Ashimori A., Matsura T., Poon D.J. J. Org. Chem. 58:1993;6949-6951
11. Gilbert J.C., Selliah R.D. Tetrahedron. 50:1994;1651-1664
12. Watanabe N., Ohtake Y., Hashimoto S., Shiro M., Ikegami S. Tetrahedron Lett. 36:1995;1491-1494
13. Overman L.E., Ashimori A., Bachad B., Calter M.A., Govek S.P., Poon D.J. J. Am. Chem. Soc. 120:1998;6488-6499
14. Overman L.E., Pavone D.V., Stearns B.A. J. Am. Chem. Soc. 121:1999;7702-7703
15. Rife J., Ortuno R.M. Tetrahedron: Asymmetry. 10:1999;4245-4260
16. Chavan, S. P.; Kamat, S. K.; Sivadasan, L.; Balakrishnan, K.; Khobragade, D. A.; Ravindranathan, T.; Gurjar, M. K.; Kalkote, U. R. U.S. Patent U.S. 6,350,912 B1 Chem. Abstr. 2002, 136, 200009
17. Dei S., Romanelli M.N., Scapecchi S., Teodori E., Chiarini A., Gualtieri J. Med. Chem. 34:1991;2219-2225
18. Floyd M.B., Weiss M.J. J. Org. Chem. 44:1979;71-75
19. Sanchez I.H., Lopez F.J., Soria J.J., Larraza M.I., Flores H.J. J. Am. Chem. Soc. 105:1983;7640-7643
20. Meyers A.I., Hanreich R., Wanner K.T. J. Am. Chem. Soc. 107:1985;7776-7778
21. Ogasawara K., Yamada O. Tetrahedron Lett. 39:1998;7747-7750
22. +), 274, 254, 218, 204, 128, 91, 70, 59