An enantioconvergent construction of the key intermediate of (+)-vincamine

Heterocycles

Volumn 42, Issue 1, 1996, Pages 65-69

  Yamane, Takahiro ^a   Ishizaki, Michiyo ^a   Suzuki, Mahito ^a   Takahashi, Michiyasu ^a   Hiroya, Kou ^a   Takano, Seiichi ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004999198     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s20     Document Type: Article

References (16)

1. S. Takano, S. Sato, E. Goto, and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1986, 156.
2. A pertinent review, see: M. Lounasmaa and A. Tolvanen, in 'The Alkaloids,' Vol. 42, ed. by G. A. Cordell, Academic Press, San Diego, 1992, pp. 1-116.
3. a) S. Takano, T. Yamane, M. Takahashi, and K. Ogasawara, Tetrahedron: Asymmetry, 1992, 3, 837.
4. b). T. Yamane, M. Takahashi, and K. Ogasawara, Synthesis, 1995, in press.
5. M. Graff, A. AlDilaimi, P. Segineau, M. Rambaud, and J. Villieras, Tetrahedron Lett., 1986, 27, 1577; J. Villieras, M. Rambaud, and M. Graff, Synth. Commun., 1986, 16, 169.
6. M. Graff, A. AlDilaimi, P. Segineau, M. Rambaud, and J. Villieras, Tetrahedron Lett., 1986, 27, 1577; J. Villieras, M. Rambaud, and M. Graff, Synth. Commun., 1986, 16, 169.
7. Y. Ueno, K. Chino, M. Watanabe, O. Moriya, and M. Okawara, J. Chem. Chem. Soc., 1982, 104, 5564.
8. cf. a) G. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720. b) G. Stork, R. Mook, Jr., S. A. Biller, and S. D. Rychnovsky, ibid., 1983, 105, 3741. c). G. Stork and P. M. Sher, ibid., 1986, 108, 303.
9. cf. a) G. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720. b) G. Stork, R. Mook, Jr., S. A. Biller, and S. D. Rychnovsky, ibid., 1983, 105, 3741. c). G. Stork and P. M. Sher, ibid., 1986, 108, 303.
10. cf. a) G. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720. b) G. Stork, R. Mook, Jr., S. A. Biller, and S. D. Rychnovsky, ibid., 1983, 105, 3741. c). G. Stork and P. M. Sher, ibid., 1986, 108, 303.
11. The epimers could be separable by silica gel column chromatography.
12. F. A. Carey and A. S. Court, J. Org. Chem., 1972, 37, 1926.
13. cf. S. Takano, S. Hatakeyama, and K. Ogasawara, J. Am. Chem. Soc., 1976, 98, 3022.
14. J. T. Gupton, D. Baran, R. Bennett, G. R. Hertel, and J. P. Idoux, Synth. Commun., 1984, 14, 1001.
15. J. Kopecky and J. Smejkal, Chem. & Ind., 1966, 1529.
16. 3) δ: 4.33 (dd, J=5.7, 2.8 Hz, 1H), 2.51-2.31 (m, 2H), 2.08-1.26 (m, 10H), 0.91 (t, J=7.3 Hz, 3H).