Synthesis and Facile One-pot Aldol/Elimination/Diels-Alder Reaction of ß-Keto-Z-Dienylamides as Cytochalasin C Intermediates¹

Abstract

The coupling of chiral dienylamine 1ZE with ß-ketoesters and subsequent one-pot aldol reaction with derivatives of glyoxylic acid, acetylation of the hydroxyester thus produced, and intramolecular Diels-Alder reaction of the diene portion of the molecule with the incipient dienophile is described. The entire sequence generates all of the requisite chiral centers in the isoindolone skeleton of cytochalasin C simultaneously, in an overall yield of approximately 85%.