Easy access to various natural keto polyunsaturated fatty acids and their corresponding racemic alcohols.

Abstract:

:Various optically active hydroxy derivatives of polyunsaturated fatty acids were easily oxidised to their corresponding keto derivatives using Dess-Martin periodinane. The reaction was run on the millimolar scale with good yields and without appreciable isomerisation of the surrounding double bonds. Reduction of these keto compounds to yield back the starting alcohols, but now as racemic mixtures, was also conducted using CeCl(3)-NaBH(4), once again without noticeable modification of the stereochemistry of the double bonds. These reactions proved the usefulness of the chemoenzymatic access to oxylipins through the use of lipoxygenases with various regiospecificity, combined with chemical transformations of the formed hydro(pero)xides.

journal_name

Chem Phys Lipids

authors

Iacazio G

doi

10.1016/s0009-3084(03)00087-2

subject

Has Abstract

pub_date

2003-10-01 00:00:00

pages

115-21

issue

2

eissn

0009-3084

issn

1873-2941

pii

S0009308403000872

journal_volume

125

pub_type

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