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

Institut für Organische Chemie, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
Organic & Biomolecular Chemistry (Impact Factor: 3.56). 07/2010; 8(14):3300-6. DOI: 10.1039/c004199h
Source: PubMed


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.

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