Abstract A short, efficient and stereoselective synthesis of enantiomerically pure (2R, 3S, 4R) 3, 4-dihydroxy-2-hydroxymethylpyrrolidine, a galactosidase inhibitor, from 4-hydroxy-L- proline is presented. The key steps are the regio-and stereoselective hydroxylation of a 4- oxoproline enolate and the stereoselective reduction of the resulting ketoalcohol. An N-(9- phenylfluoren-9-yl) moiety is used not only as an N-protecting group but as a regio-and ...
