Conversion of Beta-Lactams to Versatile Synthons via Molecular Rearrangement and Lactam Cleavage

Abstract

Substituted 6-lactams can be synthesized by a variety of methods some of which are stereocontrolled and diastereoselective.Because of their high chemical reactivity and their p~openslty for molecular rearrangement, these 6-lactams can serve as efficient syntnons lor racemio or optically active forms of diverse types of natural products such as carbohydrates, alkaloids.amino aclds and oligopeptides.TI$ Dedicated to Prof. Max Tishler on the occasion of his 80th birthday.CONTENTS A Introduotion B Rearrangement or 6-lactam Ring 1 SYnthOnS for Carbohyd~ates ii SynthOnS for Alkaloids ill Synthons for 1:)-Biotin iv Synthons for Antibiotics Y Synthons far a-Amino Acids vi Synthons for I+)-Laevigatin