Total Synthesis and Absolute Configuration of (-)-Sedacryptine

Synlett

Volumn 1996, Issue 1, 1996, Pages 100-102

  Akiyama, Eiji ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002954226     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5335     Document Type: Article

References (22)

1. Heterocycles, 1989, 28, 1229
2. (a) Hirama, M.; Shigemoto, T.; Yamazaki, Y., Itô, S. J. Am. Chem. Soc., 1985, 107, 1797.
3. (b) Hirama, M.; Shigemoto, T.; Yamazaki, Y.; Itô, S. Tetrahedron Lett., 1985, 26, 4133.
4. (c) Hirama, M.; Shigemoto, T.; Itô, S. Tetrahedron Lett., 1985, 26, 4137.
5. (d) Hirama, M.; Nishizaki, I.; Shigemoto, T.; Itô, S. J. Am.Chem.Soc., Chem. Commun., 1986, 393.
6. (e) Hirama, M.; Shigemoto, T.; Itô, S. J. Org. Chem., 1987, 29, 3342.
7. (f) Hirama. M. J. Synth. Org. Chem. Jpn., 1987, 45, 346.
8. (g) Hirama, M.; Hioki, H.; Itô, S.; Kabuto, C. Tetrahedron Lett., 1988, 29, 3121.
9. (h) Hirama, M.; Hioki, H.; Itô, S. Ibid., 1988, 29, 3125.
10. (i) Hirama, M.; Iwakuma, T.; Itô, S. J. Am. Chem. Soc., Chem. Commun., 1987, 1523.
11. Oishi, T.; Iwakuma, T.; Hirama, M.; Itô, S. Synlett, 1995, 404.
12. Hootelé, C.; Colau, B.; Halin, F. Tetrahedron Lett., 1980 21, 5061.
13. Natsume, M.; Ogawa, M. Heterocycles, 1983, 20, 601.
14. Hootelé, C.; Colau, B.; Halin, F. Tetrahedron Lett., 1980, 21, 5063.
15. Ayer, W. A.; Habgood, T. E. "The Alkaloids", Mansle, R. H. F. ed., 1968, vol 11, p 459.
16. Johnson, F. Chem. Rev., 1968, 68, 375.
17. The similar results were also reported, see: Barringer, D. F. Jr.; Berkelanammer, G.; Carter, S. D.; Goldman, L.; Lanzilotti, A. E. J. Org. Chem., 1973, 38, 1933.
18. We are grateful to Prof. K. Ogasawara for his kind gift of (R)-(-)-epichlorohydrin.
19. Takano, S.; Ogasawara, K. J. Syn. Org. Chem. Jpn. 1989, 47, 813.
20. Falck, J. R.; Yang, Y.-L. Tetrahedron Lett., 1984, 25, 3565.
21. Baker's yeast reduction of ethyl, methyl, and potasium 3-oxo-3-phenylpropanoate gave the corresponding (S)-alcohol in 61% (84% ee), 53% (97% ee), and 16% (>99% ee) yield, respectively. Also see: Hirama, M.; Shimizu, M.; Iwashita, M. J. Chem. Soc., Chem. Commun., 1983, 599; Deol, B. S.; Ridley, D. D.; Simpson, G. W. Aust. J. Chem., 1976, 29, 2459.
22. Baker's yeast reduction of ethyl, methyl, and potasium 3-oxo-3-phenylpropanoate gave the corresponding (S)-alcohol in 61% (84% ee), 53% (97% ee), and 16% (>99% ee) yield, respectively. Also see: Hirama, M.; Shimizu, M.; Iwashita, M. J. Chem. Soc., Chem. Commun., 1983, 599; Deol, B. S.; Ridley, D. D.; Simpson, G. W. Aust. J. Chem., 1976, 29, 2459.