Carbocyclic nucleoside analogs .1. Concise enantioselective synthesis of functionalized cyclopentanes and formal total synthesis of aristeromycin

An enantioselective synthesis of functionalized cyclopentanes has been used to access carbocyclic nucleoside analogs. This pathway allows access to carbocyclic C- or carbocyclic N-nucleosides from a common intermediate, ester 16. Additionally, (1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-cyclopentanemethanol (18), an intermediate in the total synthesis of aristeromycin, has been prepared as a single enantiomer in eight isolated steps from cyclopentadiene. Progress toward the synthesis of novel carbocyclic C-nucleosides is also discussed.