Asymmetric synthesis of key synthetic intermediates of Aspidosperma and Hunteria type indole alkaloids

Heterocycles

Volumn 43, Issue 8, 1996, Pages 1735-1750

  Okada, Kunisuke ^a   Murakami, Kazumasa ^a   Tanino, Hideo ^a   Kakoi, Hisae ^a   Inoue, Shoji ^a  

^a MEIJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001577212     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-96-7506     Document Type: Article

References (9)

1. a) S. Takano, M. Yonaga, M. Morimoto, and K. Ogasawara, J. Chem. Soc., Perkin Trans, 1,1985, 305.
2. b) M. Node, H. Nagasawa, and K. Fuji, J. Org. Chem., 1990, 55, 517 and references cited therein.
3. c) A. I. Meyers, J. Romine, and A. J. Robichaud, Heterocycles, 1990, 30, 339.
4. d) M. Ihara, M. Takahashi, N. Taniguchi, K. Yasui, H. Niitsuma, and K. Fukumoto, J. Chem. Soc., Perkin Trans, 1, 1991, 525.
5. a) M. Asaoka andH. Takei, Heterocycles, 1989, 29, 243.
6. b) G. Palmisano, P. D'Anniballe, and M. Santagostino, Tetrahedron, 1994, 50, 9487.
7. K. Okada, T. Katsura, H. Tanino, H. Kakoi, and S. Inoue, Chem. Lett., 1994, 157 and references cited therein.
8. 1H-nmr to be 76% ee based on two singlets appeared at 2.05 and 2.02 ppm with integral ratio of 88:12. Optical yield on the acyl migration reaction, in this case, was 84.4%.
9. Direct catalytic hydrogenation of 22 produced undesired product (23b, 50%) and alcohol (23a, 40%).