A Novel Route to Pyrimidine Nucleosides via Intramolecular Couplings of Bases with 2′-Deoxyribosides: Quick and Stereospecific...but with a 'Twist'

Abstract

Coupling of a pyrimidine base (e.g., thymine) with the C-5′ hydroxyl group of a 2′-deoxyriboside via bromoetherification leads to intermediates which can be converted to cyclonucleosides under the influence of Lewis acids. Ring opening by β-elimination affords nucleosides which are stereopure at the required anomeric position.