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

摘要

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. (C) 2016 Elsevier Ltd. All rights reserved.