A stereocontrolled method for the synthesis of d- and L-2-deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction

摘要

A novel synthetic procedure has been developed that provides access to D/L-2-deoxy-C-nucleosides from 3,4-epoxytetra-hydrofuran in seven steps and in moderate to good yields. The key chemical transformation was the Lewis acid catalysed intramolecular cyclisation reaction of an acetal for which the stereochemical outcome was dependent of the reagents' ratio.