A concise, four-step, asymmetric synthesis of a beta-lactam-based cholester
ol absorption inhibitor, Sch 57939, was developed, The discovery of a one-s
tep enantio- and diastereoselective synthesis of a trans-beta-lactam provid
ed easy access to the desired three chiral centers. A novel zinc phenoxide-
promoted ether synthesis was reported for the completion of the side chain.