Synthesis of Annulated Furanoses via Stereoselective Radical Cyclization of Haloalkenes Derived from Diacetone Glucose

Abstract

The synthesis of some cyclohexane-, cycloheptane- and tetrahydropyran-annulated furanoses via tributyltin hydride - 2,2′-azobisisobutyronitrile promoted radical cyclization of C3-branched-chain sugars 2-7, prepared from diacetone glucose (1,2:5,6-di-O-isopropylidene-α-D-glucofuranose), is described.