Radical cyclization of some unsaturated carbohydrate-derived propargyl ethers and acetals

Abstract

Treatment of propargyl ethers and acetals derived from deoxy-D-hexenopyranosides of erythro and threo configuration with tributyltin hydride with a radical initiator gave fused pyranofuranosides. This vinylic radical cyclization allowed the completely stereo- and regio-specific introduction, at the C-2 or C-3 position, of a functionalized carbon chain which can be further manipulated to create new chiral centres.