Lipase-Promoted Access to Phenolic Herbertane-Type Sesquiterpenes:(+)-l,14-Herbertenediol,(-)-a-Herbertenol,(-)-Herbertenediol and Their Enantiomers

摘要

An enantioselective synthesis of(+)-!,14-herbertenediol,and a formal enantioselective synthesis of(-)-alpha-herbertenol and(-)-herbertenediol,employing a lipase-promoted and a key stereoselective alkylation of a cyclopentane unit based methodology,are described.Molecular mechanics considerations that could account for the major role played by the substitution pattern of the benzene nucleus in the herbertane framework in comparison with those of the cuparane framework are described.