T. Akeboshi, Y. Ohtsuka, T. Sugai
Jun 25, 1998
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron
Abstract
Abstract A new approach to ethyl (2R, 3R)-2-t-butyldimethylsilyloxymethyl-3-hydroxy-2-methylbutanoate, a compound which is related to a synthetic intermediate of the side chain of furaquinocin D, is described. The characteristic feature of this compound is a quarternary chiral center and an adjacent secondary alcohol, both of which are in a stereochemically defined state, and the setup of these functionalities was achieved by a combination of stereoselective chemical and enzymatic reactions. The reduction of ethyl 2-hydroxymethyl-2-methyl-3-oxobutanoate with excess NaBH4 afforded (2R ∗ , 3R ∗ )-(±)- hydroxy ester with a high diastereomeric excess. After protecting the primary hydroxy group as TBDMS ether, the optical resolution was achieved by lipase-catalyzed hydrolysis of the corresponding chloroacetate in a highly enantioselective manner.