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Paper | Regular issue | Vol 81, No. 8, 2010, pp.1791-1798
Published online, 24th June, 2010
DOI: 10.3987/COM-09-11828
Formal Syntheses of Dihydrocorynantheine and Isorhynchophylline via Proline Catalyzed Mannich-Michael Reaction

Kazuhiro Nagata, Hitomi Ishikawa, Ayako Tanaka, Michiko Miyazaki, Takuya Kanemitsu, and Takashi Itoh*

*School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan


Proline catalyzed Mannich-Michael reaction of 3-ethyl-3-buten-2-one with 9-tosyl-3,4-dihydro-β-carboline proceeded in a highly stereoselective manner. The reaction was applied to formal syntheses of dihydrocorynantheine and isorhynchophylline.