Highly Regio- and Enantioselective Reduction of 3,5-Dioxocarboxylates

Only the keto group in position C-5 is reduced in the enzymatic reduction of 3,5-dioxocarboxylates by the alcohol dehydrogenase of Lactobacillus brevis (LBADH; see scheme). The strategy of nature for manipulating β-keto metabolites inspired the development of a chemoenzymatic approach to virtually enantiopure 3,5-dihydroxycarboxylate building blocks. The crucial enzymatic step can be performed on an attractively large scale.