Synthesis of Proposed Aglycone of Mandelalide A

A highly convergent synthesis of the proposed mandelalide A aglycone is reported. The cornerstones of the synthetic strategy include the following: E-selective intramolecular Heck cyclization, Masamune–Roush olefination, Stork–Zhao–Wittig olefination, modified Prins cyclization; Sharpless asymmetric dihydroxylation followed by Williamson-type etherification, Julia–Kocienski olefination, Brown crotylation, and Brown allylation reactions.