A new chemoenzymatic approach to the synthesis of penems

Abstract

A new synthesis of the valuable penem antibiotics FCE 22101 and FCE 22891 which does not require the use of expensive protecting groups is reported. A mixed carbon-silicon protection of two hydroxy groups was used, followed by a selective enzymatic hydrolysis of the resulting 8-O-protected-2-carboxylic ester (18). Lipase from Chromobacterium viscosum and lipoprotein lipase from Pseudomonas sp. gave excellent results in both free or immobilized form.