A convergent total synthesis of resorcylic acid lactones zeaenol and cochliomycin A

Abstract

A convergent approach for the stereoselective total synthesis of zeaenol and cochliomycin A is reported. The key steps involved are alkyne generation using Ohira-Bestmann reagent onto sugar lactol, NaH mediated one-pot esterification and acetonide deprotection, Trost’s protocol of hydrosilylation followed by protodesilylation to get exclusively E-olefin from internal alkyne and ring closing metathesis (RCM) reaction. Readily accessible d-lyxose has been utilized as the chiron substrate for generation of aliphatic chain fragment and 2,4,6-trihydroxybenzoic acid has been used for the synthesis of vinylated arene fragment.