First Total Synthesis of the Phenolic 7,8-Dihydro-8-oxoprotoberberine Alkaloid, Cerasonine

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_N2 reaction.