Solid-Phase Synthesis of Cyclic Depsipeptides Containing a Tyrosine Phenyl Ester Bond

Abstract

The first solid-phase strategy for the synthesis of cyclic depsipeptides containing a phenyl ester linkage in their structure is described. The key steps of the synthesis were the formation of the phenyl ester bond and the on-resin head-to-side-chain cyclization. The amino acid configuration significantly influenced the formation and the stability of the cyclic depsipeptides. The presence of a l-Tyr1 and a d-Tyr7 led to the most stable sequences