Synthesis and enzymatic resolution of carbocyclic 2′-ara-fluoro-guanosine: a potent new anti-herpetic agent

Abstract

(±)-Carbocyclic-9-(2′-deoxy-2′-β-fluoroarabinofuranosyl) guanine (8) and the corresponding furanose compound (12) have been synthesised; the former compound [which was resolved by formation of the monophosphate (20) and enantioselective hydrolysis using a 5′-nucleotidase] is an extremely potent inhibitor of herpes simplex viruses types 1 and 2.