CARBOCYCLIC NUCLEOSIDE ANALOGS .1. CONCISE ENANTIOSELECTIVE SYNTHESISOF 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 ac cess to carbocyclic C- or carbocyclic N-nucleosides from a common inte rmediate, ester 16. Additionally, S,4R)-4-amino-2,3-dihydroxy-1-cyclop entanemethanol (18), an intermediate in the total synthesis of arister omycin, has been prepared as a single enantiomer in eight isolated ste ps from cyclopentadiene. Progress toward the synthesis of novel carboc yclic C-nucleosides is also discussed.