SYNTHESIS OF CARBOCYCLIC ANALOGS OF GUANOSINE 5'-(BETA-L-FUCOPYRANOSYL DIPHOSPHATE) (GDP-FUCOSE) AS POTENTIAL INHIBITORS OF FUCOSYLTRANSFERASES

Two carbocyclic analogues of GDP-fucose consisting of 5a-carba-beta-L-fucopyranose and its unsaturated counterpart have been synthesized as potential inhibitors of fucosyltransferases through the intramolecular Emmons-Horner-Wadsworth olefination of the 2,6-dioxo-phosphonate derivative, readily available from L-fucose, followed by chemo- and stereoselective reductions of the alpha,beta-unsaturated inosose intermediate, which are the critical steps.