Asymmetric synthesis of sceletium alkaloids: (-)-Mesembrine, (+)- sceletium a-4, (+)-tortuosamine and (+)-N-formyltortuosamine

Tetrahedron Letters

Volumn 39, Issue 42, 1998, Pages 7747-7750

  Yamada, Osamu ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkaloids; Asymmetric synthesis; Coupling reactions; Palladium and compounds; Pyridines

Indexed keywords

ALKALOID; CYCLOHEXENE DERIVATIVE; MESEMBRINE; SCELETIUM; SCELETIUM A 4; TORTUOSAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENANTIOMER; PURIFICATION; SYNTHESIS;

EID: 0032532229     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01689-X     Document Type: Article

References (27)

1. 1. Kamikubo, T.; Ogasawara, K. Chem. Commun. 1998, 783.
2. 2. a) Popelak, A.; Lettenbauer, G. "The Alkaloids", Vol. IX, Manske, R. H. F. Ed. Academic Press, 1967, p. 467.
3. b) Jeffs, P. W.; Luhan, P. A.; McPhail, A. T.; Martin, N. H. J. Chem. Soc., Chem. Commun. 1971, 1466.
4. c) Snyckers, F. O.; Strelow, F.; Wiechers, A. J. Chem. Soc., Chem. Commun. 1971, 1467.
5. d) Luhan, P. A.; McPhail, A. T. J. Chem. Soc., Perkin Trans. 2, 1972, 2006.
6. e) Jeffs, P. W.; Capps, T.; Johnson, D. B.; Karle, J. M.; Martin, N. H.; Rauckman, B. J. Org. Chem. 1974, 39, 2703.
7. 3. Coggon, P.; Farrier, D. S.; Jeffs, P. W.; McPhail, A. T. J. Chem. Soc. (B), 1970, 1267.
8. 1H NMR and MS) and analytical (combustion and high resolution MS) data.
9. 5. For example, Yamada, O.; Ogasawara, K. Synthesis 1995, 1291.
10. 6. Enantiomeric excess was determined by hplc using a chiral column: for 8 (CHIRALCEL OD: Pr'OH-hexane, 1:9); for 9 (CHIRALCEL OD: Pr'OH-hexane, 1:4).
11. 7. (a) McIntosh, J. M.; Kiser, E. J. Synlett 1997, 1283.
12. (b) A pertinent review, see: Kolb, H. C.; Van Nieuwenhze, M, S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2482.
13. 8. Burgess, E. M.; Penton, H. R. Jr.; Taylor, E. A.; Williams, M, W. Org. Synth. Col. Vol. 1988, 6, 788.
14. 9. Oriyama, T.; Imai, K.; Sano, T.; Hosoya, T. Tetrahedron Lett. 1998, 39, 3529.
15. 10. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564.
16. 11. Stork, G.; Mook, R.; Jr. J. Am. Chem. Soc. 1983, 105, 3720.
17. 12. Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554.
18. 13. Yamane, T.; Ogasawara, K. Synlett 1996, 925.
19. 14. Grieco, P. A.; Oguri, T.; Yokoyama, Y. Tetrahedron Lett. 1978, 419.
20. 15. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171.
21. 16. The epimeric alcohol gave a complex mixture under the same dehydration conditions.
22. 17. Salmond, W. G.; Barta, M. A.; Havens, J. L. J. Org. Chem. 1978, 43, 2057.
23. 18. Takano, S.; Imamura, Y.; Ogasawara, K. Tetrahedron Lett. 1981, 22, 4479.
24. 19. Martin, S. F.; Puckette, T. A.; Colapret, J. A. J. Org. Chem. 1979, 44, 3391.
25. 20. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917.
26. 21. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
27. 22. Miller, M. W.; Johnson, C. R. J. Org. Chem. 1997, 62, 1582.