A Matteson Homologation‐Based Synthesis of Doliculide and Derivatives

Abstract

Doliculide belongs to a group of marine cyclodepsipeptides with interesting biological properties. Apart from a halogenated dipeptide, a polyketide fragment containing 5 stereogenic centers is the most eye-catching element. This building block can be synthesized in a highly stereoselective fashion using only one key reaction: the Matteson homologation. This straightforward protocol allows for the introduction of a wide range of substituents at almost any position of a growing carbon chain and it is therefore perfectly suited for the synthesis of derivatives for structure-activity relationship studies