Synthetic approach directed toward the determination of the stereochemistry of scarce natural products with potent antimitotic or cytotoxic activity

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Toward the determination of the stereochemistry of nigricanoside A, a marine-derived glycolipid bearing an unprecedented structural pattern and a potent antimitotic activity, the synthesis of its highly oxygenated alpha- and beta-fatty acid chains has been accomplished. Its southeastern segment consisting of a galactosyl glycerol unit and the right-hand portion of the bata-chain has also been synthesized. The segment is planned to connect with a northwestern segment of the target molecule by the Julia-Kocienski coupling reaction. Synthetic study on the 26-membered macrolide amphidinolide N has also been undertaken and the preparation of its C7-C13 portion has been completed by using an asymmetric vinylogous Mukaiyama aldol reaction (Kobayashi aldol reaction) as the key step.