Synthesis of C-nucleosides via radical coupling reaction

Abstract

Photolysis of O-acyl derivatives of N-hydroxy-2-thiopyridone, prepared from tetrahydrofuran-2-carboxylic acid, D-ribofuranosylmethanoic acid, and D-ribopyranosylmethanoic acid, gave the corresponding C-nucleoside derivatives in the presence of heteroaromatic compounds via radical pathways. The essential step in this method is a radical coupling reaction of D-ribofuranosyl radical or D-ribopyranosyl radical and some heteroaromatic bases. This is a new method for the preparation of C-nucleosides using sugar carboxylic acids.