Synthesis of Novel Polycyclic β-Lactams fromd-Glucose via Unusual ­Substrate-Controlled Radical Cyclization

Abstract

A highly stereoselective and substrate-controlled synthesis of polycyclic β-lactams from d-glucose derived chiral template via intramolecular free radical cyclization is described. The cyclization is highly substrate dependant, proceeding via 6-exo and 7-endo heptynyl type radical cyclization with the radical acceptor at N-1 and the radical progenitor on a sugar moiety, anchored to the β-lactam ring at C-4.