Oxidation of threo ‐9,10‐Dihydroxystearic Acid Mediated by Micrococcus luteus as a Key Step in the Conversion of Oleic Acid into Pelargonic and Azelaic Acids

A sequential one‐pot chemoenzymatic procedure for the conversion of diol 1 , easily obtained from oleic acid, into pelargonic and azelaic acids is herein described. The oxidation of diol 1 into a mixture of the corresponding regioisomeric hydroxyketones was promoted by an alcohol dehydrogenase from Micrococcus luteus , selected after an extensive screening of commercial enzyme kits and strain collections. The stereochemistry of the oxidation process of chiral diol 1 was also investigated. The hydroxyketones obtained by the biocatalyzed oxidation were submitted to further oxidative cleavage by a mild treatment with aqueous NaClO in a biphasic mixture, affording pelargonic and azelaic acids in high yield (76 and 71 %, respectively) with no need of column chromatography.