An Intramolecular Diels-alder Reaction of a Z-Diene. Generation Of The Chiral Isoindolone Nucleus Of Cytochalasin C.¹

Abstract

Aldol/elimination reactions of ß-ketoamides with methyl glyoxylate result in highly selective production of Z-α,ß-unsaturated amides. An intramolecular Diels-Alder reaction of a triply activated dienophile derived from chiral dienylamine 7ZE stereospecifically affords chiral bicyclic lactam 11 at room temperature.