Total Synthesis of Ustiloxin D
AL Brown, NL Fifer, L Hunter, QI Churches, PWH Chan, SB Cohen, CA Hutton
STRATEGIES AND TACTICS IN ORGANIC SYNTHESIS, VOL 12 | Strategies and Tactics in Organic Synthesis | ACADEMIC PRESS LTD-ELSEVIER SCIENCE LTD | Published : 2016
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.