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.