Enantiospecific synthesis of the antituberculosis marine sponge metabolite (+)-puupehenone. The arenol oxidative activation route |
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| Authors: | Quideau Stéphane Lebon Marjolaine Lamidey Anne-Marie |
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| Affiliation: | Laboratoire de Chimie des Substances Végétales, Centre de Recherche en Chimie Moléculaire, Université Bordeaux 1, 351 Cours de la Libération, F-33405 Talence, France. s.quideau@lcsv.u-bordeaux1.fr |
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| Abstract: | formula: see text] The total synthesis of the marine sesquiterpene quinone (+)-puupehenone, a promising new antituberculosis agent, was achieved in 10 steps starting from commercially available (+)-sclareolide. The key feature of this synthesis is the construction of the heterocycle via an intramolecular attack of the terpenoid-derived C-8 oxygen function onto an oxidatively activated 1,2-dihydroxyphenyl unit. |
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