An Intramolecular Case of Sharpless Kinetic Resolution: Total Synthesis of Laulimalide

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The microtubule-stabilizing antitumor agent laulimalide (1) has been obtained in by new synthetic route. The carbon skeleton was assembled by means of Julia–Kocienski (C16–C17) and Horner–Wadsworth–Emmons (C21–C22) olefinations. Still–Gennari olefination was used for the C2–C3 ring closure. The key step of the synthesis was a regioselective C16–C17 matched Sharpless asymmetric epoxidation.