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.
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Chang et al. (2005) studied this question.
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