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Enantioselective total synthesis of plakotenin, a cytotoxic metabolite from Plakortis sp.

Research paper by Stephanie S Arzt, Emmanuel E Bourcet, Thierry T Muller, Stefan S Bräse

Indexed on: 03 Jun '10Published on: 03 Jun '10Published in: Organic & Biomolecular Chemistry



Abstract

The first total enantioselective synthesis of plakotenin is described. This marine natural product was isolated from an Okinawan sponge of the genus Plakortis and shows potent biological activity against several cancerous cell lines. A biomimetic intramolecular Diels-Alder reaction served as a key step in the total synthesis. The synthesis proves the relative and absolute stereochemistry of natural plakotenin.