Enantioselective total synthesis of plakotenin, a cytotoxic metabolite from Plakortis sp.
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.
Arzt
Stephanie
S
Institut für Organische Chemie, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
Bourcet
Emmanuel
E
Muller
Thierry
T
Bräse
Stefan
S
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D045744:Cell Line, Tumor; D047229:Plakortis / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000970:Antineoplastic Agents; D002264:Carboxylic Acids; C400358:plakotenin