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First Enantiospecific Synthesis of the Antitumor Marine Sponge Metabolite (−)-15-Oxopuupehenol from (−)-Sclareol

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journal contribution
posted on 14.04.2005 by E. J. Alvarez-Manzaneda, R. Chahboun, I. Barranco Pérez, E. Cabrera, E. Alvarez, R. Alvarez-Manzaneda
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.