Chemical & Pharmaceutical Bulletin 2008-07-01

First total synthesis of the phenolic 7,8-dihydro-8-oxoprotoberberine alkaloid, cerasonine.

Thanh Nguyen Le, Won-Jea Cho

Index: Chem. Pharm. Bull. 56(7) , 1026-9, (2008)

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Abstract

First total synthesis of the phenolic protoberberine, cerasonine, was accomplished through a coupling reaction between o-toluamide and benzonitrile. This key step provided the 3-arylisoquinoline which was then successfully converted to 7,8-dihydro-8-oxoprotoberberine through an intramolecular S(N)2 reaction.