New cleavage approaches to combinatorial synthesis of homoserine lactones

Abstract

The polymer-supported synthesis of a methionine-functionalized resin for new cleavage strategy and combinatorial library of homoserine lactone analogs is described. The process consists of the coupling of N-Fmoc-methionine followed by deprotection to give a free amine of methionine-functionalized resin (3). After the coupling with a carboxylic acid, the final cleavage step proceeds through a BrCN-mediated cyclization process to produce homoserine lactone libraries (5) with retention of stereochemistry.