Total Synthesis of (+)-Macquarimicin A

Abstract

The first total synthesis and determination of the absolute configuration of (+)-macquarimicin A (1), a novel inhibitor of neutral sphingomyelinase (N-SMase) possessing an anti-inflammatory activity, have been accomplished. The present total synthesis features the construction of the unique tetracyclic framework via a stereoselective transannular Diels–Alder reaction, which is based on a plausible biosynthetic pathway to 1.