Enantiospecific syntheses of the methylene-and α-fluoromethylene-phosphonate analogues of 3-phospho-D-glyceric acid

Abstract

An enantioselective synthesis is described for the preparation of 2-(R)-3-carboxy-3-hydroxypropane-1-phosphonic acid (1), an isosteric analogue of 3-phospho-D-glyceric acid (2), from D-lyxose; the route is extended to provide a stereoselective synthesis of one diastereoisomer of 2-(R)-3-carboxy-1-fluoro-3-hydroxypropane-1-phosphonic acid (3), of undetermined stereochemistry at C-1; these preparations provide the first examples of syntheses of phosphonate analogues of 3-phospho-D-glyceric acid having the natural configuration at C-2.