Total Synthesis of Ustiloxin D

Abstract

This account describes the total synthesis of ustiloxin D. A first-generation, chiral pool approach to the functionalized isoleucine precursor was unsuccessful but yielded several interesting observations. A revised strategy was devised in which the concise, high-yielding total synthesis was facilitated by two key processes: an asymmetric allylic alkylation to construct the alkyl–aryl ether and an ammonia–Ugi reaction to construct the isoleucine-containing tripeptide fragment.