Synthesis of (+)-hupeol from (-)-cytisine: Transformation of a cyclic imine into a cyclic hemiacetal

Heterocycles

Volumn 53, Issue 3, 2000, Pages 545-548

  Wang, Yong Hong ^a   Higashiyama, Kimio ^a   Kubo, Hajime ^a   Li, Jia Shi ^b   Ohmiya, Shigeru ^a  

^a HOSHI UNIVERSITY   (Japan)

^b BEIJING UNIVERSITY OF CHINESE MEDICINE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; CYSTINE; HETEROCYCLIC COMPOUND; IMINE;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034162244     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8812     Document Type: Article

References (9)

1. Y. H. Wang, H. Kubo, K. Higashiyama, H. Komiya, J. S. Li, and S. Ohmiya, J. Chem. Res. (S), 1998, 196; Y. H. Wang, J. S. Li, K. Higashiyama, H. Kubo, and S. Ohmiya, Chem. Pharm. Bull., 1999, 47, 1308.
2. Y. H. Wang, H. Kubo, K. Higashiyama, H. Komiya, J. S. Li, and S. Ohmiya, J. Chem. Res. (S), 1998, 196; Y. H. Wang, J. S. Li, K. Higashiyama, H. Kubo, and S. Ohmiya, Chem. Pharm. Bull., 1999, 47, 1308.
3. A. Rieche and E. Schmitz, Chem. Ber., 1956, 89, 1254.
4. J. Quick and R. Oterson, Synthesis, 1976, 745.
5. H. Kubo, S. Ohmiya, and I. Murakoshi, Can. J. Chem., 1994, 72, 214; F. Bohlmann, E. Winterfeldt, H. Overwien, and H. Pagel, Chem. Ber., 1962, 95, 944.
6. H. Kubo, S. Ohmiya, and I. Murakoshi, Can. J. Chem., 1994, 72, 214; F. Bohlmann, E. Winterfeldt, H. Overwien, and H. Pagel, Chem. Ber., 1962, 95, 944.
7. 2 from HRMS, found 206.1058, calcd for 206.1056. MS (EI, 70eV): m/z (%) 206 (35), 177 (10), 160 (12), 148 (100), 146 (10), 134 (14).
8. S. Ohmiya, K. Saito, and I. Murakoshi, 'The Alkaloids: Lupine Alkaloids,' Vol. 47, ed. by G. A. Cordell, Academic Press, New York, 1995, pp. 1-114.
9. J. C. Pelletier and M. P. Cava, J. Org. Chem., 1987, 52, 616.