2',3'-Didehydro-2,3-dideoxy-5-fluorocytidine (DD4FC) is an anti-HIV agent currently under phase II clin. trial (Pharmaset Inc). Its mol. architecture is suitable for a Ferrier rearrangement kind of operation on a furanoid glycal to fix the position of the double bond and the relative stereochem. Despite the fact that classical Ferrier rearrangement does not work on furanoid glycals, a palladium mediated modified protocol has been developed for the glycosidation of an aromatization prone xylo-furanoid glycal for the synthesis of D-D4FC.