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Note | Regular issue | Vol 65, No. 2, 2005, pp.395-402
Published online, 10th December, 2004
DOI: 10.3987/COM-04-10274
Synthesis of Lupinine

Meng-Yang Chang,* Huo-Mu Tai,* Ching-Han Lin, and Nein-Chen Chang

*Department of Applied Chemistry, National University of Kaohsiung, No. 700 Kaohsiung University Rd., Nan-Tzu District, Kaohsiung 811, Taiwan, R.O.C.

Abstract

A synthesis of lupinine (1a) is performed from 5-amino-1-pentanol in ten steps. The glutarimide (3) was obtained from 1-(5-hydroxypentyl)-2- (4-methylphenylsulfonyl)acetamide (5) and acrylate (4) via a formal [3+3] annulation. This formation of quinolizidine skeleton was established via a key acid-catalyzed cyclization method.