Enantioselective synthesis of peperomins A, C, D, and analogs — Examination of diastereoselective cuprate conjugate additions to N-enoyl-4-diphenylmethyl-2-oxazolidinones

Abstract

A concise and general route to secolignans has been developed. The first total synthesis of secolignans peperomin A (1a), peperomin C (1b), and peperomin D (1c) was accomplished in ~28% overall yield over five synthetic steps. Peperomin analogs (1d) and (1e), possessing two differentially substituted aryl groups, were synthesized by a highly selective conjugate addition. The overall yield for the analogs 1d and 1e were 27 and 26%, respectively.Key words: peperomins, secoliganans, conjugate additions, 4-diphenylmethyl-oxazolidin-2-one.