Biomimetic Total Synthesis of (-)-Aplysistatin

Abstract

A biomimetic synthesis of (-)-aplysistatin (1) is described. The Wittig reaction of the keto ester 5 with homogeranyl triphenylphosphonium ylid gave the desired intermediate 3. Successive treatment of 3 with activated manganese dioxide, sodium chlorite and aq. trifluoroacetic acid led to the unsaturated β-hydroxy lactone 2, which was subjected to brominative cyclization to yield (-)-aplysistatin (1). © 1984, Japan Society for Bioscience, Biotechnology, and Agrochemistry. All rights reserved.