Diastereoselective synthesis of L-(+)-homolamivudine

Article abstract of DOI:10.1016/S0040-4039(99)01935-8

L-homolamivudine (2a, (2R,5R)-(+)-cis-5-(1-cytosinylmethyl)-2-hydroxymethyl-1,3-oxathiolane) and its 5-fluoro congener (2b, L-homoFTC) have been prepared from (R)-glycidol by diastereoselective synthesis. Enantioselectivity resulted from stereoselective cyclothioacetalization that preferentially gave the (2R,5R)-cis-2,5-disubstituted-1,3-oxathiolane (5), cis/trans = 5.7.