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

Alvarez-Manzaneda, E. J.; Chahboun, R.; Barranco Pérez, I.; Cabrera, E.; Alvarez, E.; Alvarez-Manzaneda, R.

doi:10.1021/ol047332j.s001

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

2005-04-14T00:00:00Z (GMT) 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.

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diastereoselective puupehenone Utilizing cyanopuupehenone drimenylphenol oxopuupehenol Antitumor enantiospecific synthesis Sclareol Oxopuupehenol Marine Metabolite antitumor antimalarial sclareol palladium First Enantiospecific Synthesis metabolite bioactive cyclization synthese puupehedione

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

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