M. Blanco, F. Sardina
Nov 7, 1994
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron Letters
Abstract
Abstract A short, efficient and stereoselective synthesis of enantiomerically pure (2 R , 3 S , 4 R ) 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 stereochemical control element as well.