Use of a cyclic sulfite as an epoxide surrogate in the regioselective synthesis of a carbocyclic ring-enlarged 4′,1'a-methano oxetanocin analogue

Abstract

Although cyclic sulfites are less reactive than their cyclic sulfate counterparts, the present work shows that cyclic sulfite 15a is a useful synthon for the convergent synthesis of carbocyclic nucleosides. Target compound 6, which represents a rigid carbocyclic nucleoside mimic of anti-HIV active 9-[2',3'-dideoxy-3'-C-(hydroxyrnethyl)-β-erythro-pentofuranosyl]adenine (3), was obtained after regioselective ring opening of 15a with adenine and radical-induced deoxygenanon of the extra hydroxyl group. Elsevier Science Ltd.