Synthesis of (±)-2′,3′-didehydro-2′,3′-dideoxy nucleosides via a modified Prins reaction and palladium(0) catalysed coupling

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Abstract
Cyclopentenyl allylic acetates have been prepared in diastereoisomerically enriched form by modification of the Prins reaction. Palladium(0) catalysed coupling between these allylic acetates and a heteroaromatic base provides a highly convergent and direct route for synthesising carbocyclic 2′,3′-didehydro-2′,3′-dideoxy nucleosides. The method is exemplified by the coupling reaction with adenine which yields (±)-2′,3′-didehydro-2′,3′-dideoxyaristeromycin 5′-O-acetate 22 in 50% yield. This has been converted in two steps into (±)-aristeromycin triacetate 5.