%0 Journal Article %A Alvarez-Manzaneda, E. J. %A Chahboun, R. %A Barranco Pérez, I. %A Cabrera, E. %A Alvarez, E. %A Alvarez-Manzaneda, R. %D 2005 %T First Enantiospecific Synthesis of the Antitumor Marine Sponge Metabolite (−)-15-Oxopuupehenol from (−)-Sclareol %U https://acs.figshare.com/articles/journal_contribution/First_Enantiospecific_Synthesis_of_the_Antitumor_Marine_Sponge_Metabolite_15_Oxopuupehenol_from_Sclareol/3291319 %R 10.1021/ol047332j.s001 %2 https://acs.figshare.com/ndownloader/files/5129059 %K diastereoselective %K puupehenone %K Utilizing %K cyanopuupehenone %K drimenylphenol %K oxopuupehenol %K Antitumor %K enantiospecific synthesis %K Sclareol %K Oxopuupehenol %K Marine %K Metabolite %K antitumor %K antimalarial %K sclareol %K palladium %K First Enantiospecific Synthesis %K metabolite %K bioactive %K cyclization %K synthese %K puupehedione %X A new route toward puupehenone-related bioactive metabolites from (−)-sclareol, based on the palladium(II)-mediated diastereoselective cyclization of a drimenylphenol, is described. Utilizing this, the first enantiospecific synthesis of the antitumor and antimalarial (−)-15-oxopuupehenol, together with improved syntheses of (+)-puupehenone, (+)-puupehedione, and (+)-15-cyanopuupehenone, were accomplished. %I ACS Publications