This document summarizes the convergent stereoselective synthesis of (-)-deoxypukalide, the enantiomer of a degradation product of the natural product pukalide. Key steps include a novel intraannular furan synthesis using a 4-oxopropargylic β-keto ester and silica gel to form a 3-carboxy 2,5-bridged furan in 96% yield. The synthesis features a "furan-last" strategy employing molecular mechanics ca
