Asymmetric total synthesis of paecilomycin F, cochliomycin C, zeaenol, 5-bromo-zeaenol and 3,5-dibromo-zeaenol by Heck coupling and late stage macrolactonization approach

Abstract

Asymmetric total synthesis of five structurally related naturally occurring 14-membered ring resorcylic acid lactones (RALs) have been described in this article through a concise and flexible way. The main highlight of the reported synthetic strategy involves successful application of an atom economical and highly stereoselective Heck reaction. Substrate directed Barbier propargylation, E-selective cross metathesis (CM) reaction, Mitsunobu esterification and late stage electrophilic halogenation reaction are the other key steps used for the total synthesis of the target molecules.