Yuan-Ching P. Chiang

Synthesis of δ-lactone, oxetane and azetidinone analogs from the naturally occurring β-lactone L-659,699. The preparation of a novel HMG CoA synthase inhibitor.

Abstract A series of δ-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 β-lactone HMG CoA synthase inhibitors.