Selective Ring-opening Fluorination of Epoxide: An Efficient Synthesis of 2'-C-Fluoro-2'-C-methyl Carbocyclic Nucleosides

Abstract

An efficient synthetic route of novel 2′(α)-C-fluoro-2′(β)-C-methyl carbocyclic nucleoside analogues is described. The key fluorinated intermediate 7 was prepared from the epoxide intermediate 5 via selective ring-opening of epoxide. Coupling of 7 with nucleosidic bases under the Mitsunobu reactions followed by deprotection afforded the target carbocyclic nucleoside analogues. The synthesized compounds were evaluated as inhibitors of the hepatitis C virus (HCV) in Huh-7 cell line in vitro.