Synthesis of HC-Toxin via Matteson Homologation and C–H Functionalization

Abstract

A new synthetic route toward host-specific HC-toxin was developed. The HC-toxin belongs to a group of cyclic, tetrapeptide histone deacetylase inhibitors containing the unusual amino acid Aeo. Key steps in the synthesis of this building block include the Matteson homologation to generate the stereogenic centers in the side chain and a C–H functionalization to connect the side chain to a protected alanine.