Stereoselective Total Synthesis of Umuravumbolide

A simple and efficient stereoselective total synthesis of desacetylumuravumbolide (1a) and umuravumbolide (1b), starting from commercially available valeraldehyde has been described. The synthetic strategy involves a highly enantioselective zinc-mediated addition of protected 2 alkyn-1-ol to aldehyde, a Crimmins aldol reaction, and Horner-Wadsworth-Emmons olefination as key steps.