SYNTHESIS OF DELTA-LACTONE, OXETANE AND AZETIDINONE ANALOGS FROM THE NATURALLY-OCCURRING BETA-LACTONE L-659,699 - THE PREPARATION OF A NOVEL HMG COA SYNTHASE INHIBITOR

A series of delta-lactone (1 and 2), oxetane (3) and azetidinone (4 and 5) analogs were prepared from the HMG CoA synthase inhibitor L-659,699 ((E,E)-11-[3'R-(hydroxymethyl)-4'-oxo-2'R-oxetanyl]-3,5,7R-trimethyl-2,4-undecadienoic acid 1,2), which maintained the trans relationship of the ring side chains. The N-tosyl azetidinone analog represents the first reported member of a new series of non beta-lactone HMG CoA synthase inhibitors.