Reactivity Parameters of the Metal Assisted 1,2-Cleavage of Penicillins

Abstract

A straightforward and smooth conversion of penicillins into l,2-secopenicillanates is described.The thiazolidine ring opening is brought about by the co-operative effect of strong non-nucleophilic bases and rhiophiiic heavy metal salts.The nature of the latter and the polarity of the solvent profoundly affect the reaction rate.nest general conditions can be drawn for che conversion of numerous 6-substituted penicillanates with various protecting groups on the carboxy function.Recently w e ' reported the shortest synthesis of penems from a natural substrate.