Total synthesis of (±)-chondrosterin I using a desymmetric aldol reaction

Abstract

The first total synthesis of racemic chondrosterin I was accomplished. The synthetic features include a Michael addition to incorporate a nitro alkane moiety, an oxidative Nef reaction, intramolecular cyclization of the γ-ketoester derivative, and a desymmetric intramolecular aldol reaction of the meso diketoester compound. The present strategy will be applicable to the synthesis of an optically active form by asymmetric desymmetrization.