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Paper | Regular issue | Vol 55, No. 5, 2001, pp.861-871
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9080
Simple Synthesis of (±)-Epibatidine

Balaram Roy, Hidenori Watanabe, and Takeshi Kitahara*

*Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan

Abstract

Concise synthesis of racemic epibatidine (1), a non-opioid analgesic alkaloid, was accomplished starting from 6-chloropyridyl-3-carbaldehyde (6) via Robinson annulation for the construction of the skeleton, by introduction of amino group through Curtius rearrangement and finally by cyclization.