Opening of aryl-substituted epoxides to form quaternary stereogenic centers: Synthesis of (-)-mesembrine

Journal of Organic Chemistry

Volumn 70, Issue 19, 2005, Pages 7711-7714

  Taber, Douglass F ^a   He, Yigang ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ARYL-SUBSTITUTED EPOXIDES; EPOXIDATION; GRIGNARD REAGENT; QUATERBARY STEREOGENIC CENTRES;

EPOXY RESINS;

ALKENE; CYCLOALKANONE; EPOXIDE; MESEMBRINE; SEROTONIN UPTAKE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DEHYDRATION; ENANTIOMER; EPOXIDATION; GRIGNARD REACTION; REACTION ANALYSIS; SYNTHESIS;

INDOLE ALKALOIDS; STEREOISOMERISM;

EID: 24944509594     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0511039     Document Type: Article

References (40)

1. For reviews on the enantioselective construction of quaternary stereogenic centers, see: (a) Martin, S. F. Tetrahedron 1980, 36, 419.
2. (b) Fuji, K. Chem. Rev. 1993, 93, 2037.
3. (c) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
4. (d) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591.
5. (e) Dennisova, I.; Barriault, L. Tetrahedron 2003, 59, 10105.
6. (f) Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363.
7. For the isolation and structural determination of (-)-mesembrine, see: (a) Popelak, A.; Haack, E.; Lettenbauer, G.; Spingler, H. Naturwissenschaften 1960, 47, 156.
8. (b) Smith, E.; Hosansky, N.; Shamma, M.; Moss, J. B. Chem. Ind. 1961, 402.
9. For leading references to previous enantioselective syntheses of (-)-mesembrine, see: (a) Takano, S.; Imamura, Y.; Ogasawara, K. Tetrahedron Lett. 1981, 22, 4479.
10. (b) Takano, S.; Samizu, K.; Ogasawara, K. Chem. Lett. 1990, 1239.
11. (c) Fukumoto, K.; Tanabe, T.; Nemoto, H. J. Org. Chem. 1995, 60, 6785.
12. (d) Mori, M.; Kuroda, S.; Zhang, C.; Sato, Y. J. Org. Chem. 1997, 62, 3263.
13. (e) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675.
14. (f) Langlois, Y.; Dalko, P. I.; Brun, V. Tetrahedron Lett. 1998, 39, 8979.
15. (g) Ogasawara, K.; Yamada, O. Tetrahedron Lett. 1998, 39, 7747.
16. (h) Taber, D. F.; Neubert, T. D. J. Org. Chem. 2001, 66, 143.
17. For leading references to previous enantioselective syntheses of (+)-mesembrine, see: (i) Meyers, A. I.; Hanreich, R.; Wanner, K. T. J. Am. Chem. Soc. 1985, 107, 7776.
18. (j) Kosugi, H.; Miura, Y.; Kanna, H.; Uda, H. Tetrahedron: Asymmetry 1993, 4, 1409.
19. For leading references to the synthesis of racemic mesembrine, see: (a) Chavan, S. P.; Khobragade, D. A.; Pathak, A. B.; Kalkote, U. R. Tetrahedron Lett. 2004, 45, 5263.
20. (b) Kulkarni, M. G.; Rasne, R. M.; Davawala, S. I.; Doke, A. K. Tetrahedron Lett. 2002, 43, 2297.
21. (c) Rigby, J. H.; Dong, W. Org. Lett. 2000, 2, 1673.
22. For cultural background and some limited activity trials of Sceletium tortuosum, see: Smith, M. T.; Crouch, N.; Gericke, N.; Hirst, M. J. Ethnopharmacol. 1996, 50, 119.
23. For the in vitro and in vivo activity of (-)-mesembrine, see: Gericke, N. P.; VanWyk, B.-E. PCT Int. Appl., WO 9746234 CAN 128: 80030, 1997.
24. Taber, D. F.; He, Y.; Xu, M. J. Am. Chem. Soc. 2004, 126, 13900.
25. For reports of the opening of arene-activated trisubstituted epoxides at the more substituted carbon to establish a quaternary center, see: (a) Gerteisen, T. J.; Kleinfelter, D. C. J. Org. Chem. 1971, 36, 3255.
26. (b) Krause, N.; Seebach, D. Chem. Ber. 1988, 121, 1315.
27. (c) Kauffmann, T.; Neiteler, C.; Robbe, S. Chem. Ber. 1992, 125, 2409.
28. (d) Jansen, J.; Knopp, M.; Amberg, W.; Bernard, H.; Koser, S.; Müller, S.; Münster, I.; Pfeiffer, T.; Riechers, H. Org. Process Res. Dev. 2001, 5, 16.
29. (a) For the preparation of the alkenes corresponding to 5a and 5c, see: Balsamo, A.; Crotti, P.; Macchia, B.; Macchia, F. Tetrahedron 1973, 29, 2183.
30. (b) For the preparation of the alkenes corresponding to 5b and 5c, see: Doan, L.; Bradley, K.; Gerdes, S.; Whalen, D. L. J. Org. Chem. 1999, 64, 6227.
31. For the preparation of 5d, see: Hoshino, O.; Sawaki, S.; Shimamura, N.; Onodera, A.; Umezawa, B. Chem. Pharm. Bull. 1987, 35, 2734.
32. We found that the sensitive epoxides could be prepared efficiently from the alkenes with dimethyl dioxirane: Murray, R. W.; Singh, M. Org. Synth. 1997, 74, 91.
33. Newbold, R. C.; Shih, T. L.; Mrozik, H.; Fisher, M. H. Tetrahedron Lett. 1993, 34, 3825.
34. Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
35. Sousa, J. A.; Bluhm, A. C. J. Org. Chem. 1960, 25, 108.
36. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454.
37. (a) Trost, B. M.; Pissot-Soldermann, C.; Chen, I.; Schroeder, G. M. J. Am. Chem. Soc. 2004, 126, 4480.
38. (b) Trost, B. M.; Xu, J. J. Am. Chem. Soc. 2005, 127, 2846.
39. (a) Aahman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918.
40. (b) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261.