An efficient, convergent approach for the total synthesis ofmicrocarpalide (1) is described. The synthetic strategyfeatures the Sharpless asymmetric dihydroxylation, regioselective epoxide opening with various nucleophiles such asa lithium acetylide and cuprates derived from the vinylstannane and the vinyl iodide for the construction of a C7−C8 trans-double bond and Yamaguchi macrolactonization asthe key steps.