Concise Asymmetric Total Synthesis of 9-epi-Sessilifoliamide J

Abstract

A 10-step asymmetric synthesis of 9-epi-sessilifoliamide J (20), together with sessilifoliamide J (6), has been accomplished from the key chiral building block 11 via a threo-selective vinylogous Mannich reaction and a Ley oxidation-SmI(2)-mediated coupling lactoniation. The absolute configuration of the natural sessilifoliamide J was established.