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Plants-mediated reduction in the synthesis of homochiral secondary alcohols

By BRUNI R., FANTIN G., MAIETTI S., MEDICI A., PEDRINI P. and SACCHETTI G.

Abstract

The reduction of 5-hexen-2-one 1, 6-methyl-5-hepten-2-one 2, acetophenone 3, cis-bicyclo[3.2.0]hept-2-en-6-one 4 and 2-methylcyclohexanone 5 with various commercially available plants (i.e., Brassica oleracea botrytis, Cucurbita maxima, Cucurbita pepo, Cynara scolimus, Daucus carota, Foeniculum vulgare and Musa sapientum) is reported. In the reduction of ketones 1-3, both (S)- and (R)-enantiomers 6-8 were obtained in good yields and with appreciable enantiomeric excesses. With racemic ketones 4 and 5, both the diastereomeric endo/exo 9 and 10 and cis/trans 11 and 12 are produced with variable yields and enantiomeric excesses depending on the various plants used

Topics: Plants-mediated biotransformation, reduction, synthesis of homochiral alcohols
Year: 2006
DOI identifier: 10.1016/j.tetasy.2006.07.029
OAI identifier: oai:iris.unife.it:11392/471450
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