A short and novel synthesis of carbocyclic nucleosides and 4'-epi-carbocyclic nucleosides from 2-cyclopenten-1-ones

Abstract Carbocyclic nucleoside analogues remain interesting target molecules having the potential to combine biological activity with greater metabolic stability than their sugar counterparts. This paper describes a rapid and versatile synthetic approach to such compounds based on commercial cyclopentenones (e.g., 1 ) that has been developed in our laboratory. Carbocyclic nucleosides like 2′-methyl-aristeromycin 6 were synthesized in racemic form in 5 steps via key intermediate 4 . The procedure was also adapted to the preparation of 4′-epi-carbocyclic nucleosides using epoxide 17 instead of 4 and employing the same methodology.