Stereoselective Synthesis of Tropane Alkaloids: Physoperuvine and Dihydroxytropanes

Synlett

Volumn 1996, Issue 8, 1996, Pages 785-786

  Majewski, Marek ^a   Lazny, Ryszard ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001131586     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5532     Document Type: Article

References (20)

1. Recent review: Lounasmaa, M.; Tamminen, T. The Alkaloids, 1993, 44, 1. Physoperuvine: McPhail, A. T.; Pinder, A. R. Tetrahedron 1984, 40, 1661.; Pinder, A. R. J. Org. Chem. 1982, 47, 3607.; Sahai, M.; Ray, A. B. ibid. 1980, 45, 3265.
2. Recent review: Lounasmaa, M.; Tamminen, T. The Alkaloids, 1993, 44, 1. Physoperuvine: McPhail, A. T.; Pinder, A. R. Tetrahedron 1984, 40, 1661.; Pinder, A. R. J. Org. Chem. 1982, 47, 3607.; Sahai, M.; Ray, A. B. ibid. 1980, 45, 3265.
3. Recent review: Lounasmaa, M.; Tamminen, T. The Alkaloids, 1993, 44, 1. Physoperuvine: McPhail, A. T.; Pinder, A. R. Tetrahedron 1984, 40, 1661.; Pinder, A. R. J. Org. Chem. 1982, 47, 3607.; Sahai, M.; Ray, A. B. ibid. 1980, 45, 3265.
4. Recent review: Lounasmaa, M.; Tamminen, T. The Alkaloids, 1993, 44, 1. Physoperuvine: McPhail, A. T.; Pinder, A. R. Tetrahedron 1984, 40, 1661.; Pinder, A. R. J. Org. Chem. 1982, 47, 3607.; Sahai, M.; Ray, A. B. ibid. 1980, 45, 3265.
5. a. Majewski, M.; Lazny, R. J. Org. Chem. 1995, 60, 5825.
6. b. Enantioselective deprotonation was reviewed: Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1.;
7. Majewski, M. in Advances in Carbanion Synthesis, Snieckus, V,. Ed.; JAI Press: Greenwich, CT, vol.3, in press.
8. a. Majewski, M.; Zheng, G.-Z. Synlett 1991, 173.
9. b. This reaction had also been independently reported in a lecture: Simpkins, N. S. Chem. Soc. Rev. 1990, 19, 335.
10. Tropane alkaloid numbering is used in this paper (cf., ref. 1).
11. Corey, E. J.; Cheng, X. M. The Logic of Chemical Synthesis; Wiley: New York, 1989.
12. Wharton, P. S.; Bohlen, D. H. J. Org. Chem. 1961, 26, 3615.
13. Wasson, R. L.; House, H. O. Org. Synth. Coll. Vol. 4, 1963, 552.
14. Boyer, F.-D.; Ducrot, P.-H.; Henryon, V.; Lallemand, J.-Y. Synlett 1992, 357.
15. Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226
16. Page, P. C. B; McCarthy, T. J. in Comprehensive Organic Synthesis, Ley S. V., Ed., Pergamon: Oxford, 1991, vol. 7, 83.
17. Bick, I. R. C.; Gillard, J. W.; Leow, H.-M.; Preston, N. W. Aust. J. Chem. 1979, 32, 2071.
18. a. Muraoka, O.; Okumura, K.; Maeda, T.; Tanabe, G.; Momose, T. Tetrahedron: Asymmetry, 1994, 5, 317.
19. b. Momose, T.; Toyooka, N.; Seki, S.; Hirai, Y. Chem. Pharm. Bull., 1990, 38, 2072.
20. c. Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett., 1990, 1319.