Base-Catalyzed Reactions of Dihydromethylenomycin A and Its Derivatives

Abstract

Derivatives of dihydromethylenomycin A undergo a facile cleavage of the five-membered ring ketone and a subsequent reclosure to give 3 (2H)-furanone derivatives under weakly basic conditions such as in the presence of K₂CO₃. The structure of a typical product was unequivocally determined by synthesis. The reaction mechanism is discussed.