Enantiospecific synthesis of the antituberculosis marine sponge metabolite (+)-puupehenone. The arenol oxidative activation route.
[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.
Quideau
Stéphane
S
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
Lebon
Marjolaine
M
Lamidey
Anne-Marie
AM
D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis*; D004224:Diterpenes / Q000737:chemistry; D010084:Oxidation-Reduction; D011161:Porifera / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D044004:Xanthones
D000995:Antitubercular Agents; D004224:Diterpenes; D012717:Sesquiterpenes; D044004:Xanthones; C109395:sclareolide; C053594:puupehenone