(-)-Zampanolide, isolated from Fasciospongia rimosa in 1996 by Tanaka and co-workers, is a 20-membered macrolactone containing a cis-2,6-disubstituted tetrahydropyran, ample unsaturation, and an unusual N-acyl hemiaminal side chain. This structurally unique polyketide exhibits significant cytotoxicity in the low nanomolar range against various tumor cell lines and induces microtubule bundles in cells. As of recently, only small amounts of (-)-zampanolide have been provided by total synthesis or extraction from its marine host. As a result, we have undertaken the large-scale preparation of this potent polyketide using electrophile-induced ether transfer methodology developed within our lab to supply material for biological studies. Advances towards this goal will be presented.

Progress towards the total synthesis of (-)-zampanolide

243rd National Meeting (2012)

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