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. 2003 Oct 17;68(21):8268-71.
doi: 10.1021/jo0348726.

A facile asymmetric route to (-)-aphanorphine

Hongbin Zhai  1 , Shengjun Luo, Chengfeng Ye, Yongxiang Ma
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A facile asymmetric route to (-)-aphanorphine

Hongbin Zhai et al. J Org Chem. .

Abstract

8O-methylaphanorphine was synthesized from 4-methoxyphenylacetaldehyde in 36% overall yield and in nine steps, featuring the formation of ring B via a Friedel-Crafts alkylative cyclization with the concomitant stereospecific introduction of the benzylic quaternary carbon center. The current work constitutes an efficient enantioselective formal synthesis of 3-benzazepine marine alkaloid (-)-aphanorphine.

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