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Paper | Special issue | Vol 70, No. 1, 2006, pp.335-344
Published online, 17th October, 2006
DOI: 10.3987/COM-06-S(W)29
Enantioselective Synthesis of ent-Sedridine and (+)-Coniine via Proline-Catalyzed Mannich Reaction

Kazuhiro Nagata, Kosuke Nishimura, Masashi Yokoya, and Takashi Itoh*

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

Abstract

Proline-catalyzed three component Mannich reaction using 5-hydroxypentanal as a substrate was achieved in high enantioselectivity to construct a chiral center at C-2 position of 2-substituted piperidine alkaloids. The method was applied to the total syntheses of ent-sedridine and (+)-coniine.