Asymmetric Synthesis of (−)-6′-β-Fluoro-aristeromycin via Stereoselective Electrophilic Fluorination

(−)-6′-β-Fluoro-aristeromycin (<b>2</b>), a potent inhibitor of <i>S</i>-adenosylhomocysteine (AdoHcy) hydrolase, has been synthesized via stereoselective electrophilic fluorination followed by a purine base build-up approach. Interestingly, purine base condensation using a cyclic sulfate resulted in a synthesis of (+)-5′-β-fluoro-isoaristeromycin (<b>2a</b>). Computational analysis indicates that the fluorine atom controlled the regioselectivity of the purine base substitution