Synthesis of Fluorinated Nucleosides

Abstract

Two practical synthetic approaches to the production of lodenosine [FddA, 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine] via 6-chloropurine riboside or 6-chloropurine 3'-deoxyriboside are described. The reaction sequence contains new fluorination methods and new applications of radical reduction. The reagents and reaction conditions of each step have been carefully selected to ensure robustness and safety.