Stereocontrolled synthesis of O- and C-furanosides through 1,4-iodocyclisation of d-galactal

Iodocyclisation of 6-O-protected-D-galactal, followed by radical reduction, gives [2.2.1] bicyclic acetals which are regioselectively opened by various nucleophiles (alcohols, allyltrimethylsilane, triphenylphosphine) to give furanosyl compounds.