Synthetic Study of Macquarimicins:  Highly Stereoselective Construction of the AB-Ring System

The highly stereoselective synthesis of the AB-ring system of macquarimicins, a novel class of microbial metabolites with inhibitory activity for neutral sphingomyelinase, has been achieved. The present synthesis features the highly stereocontrolled construction of the cis-tetrahydroindan structure via the intramolecular Diels−Alder reaction of an (E,Z,E)-1,6,8-nonatriene derived from d-glyceraldehyde acetonide.