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. © 2008 Pharmaceutical Society of Japan.