PHOSPHONATE ANALOGS OF CARBOCYCLIC NUCLEOTIDES

Cyclopentadiene was converted in six steps to the key intermediate a,2 beta,4alpha)-4-amino-2-(benzyloxy)cyclopentanol (10), which in turn wa s converted to the carbocyclic nucleoside analogs 14 and 19 by standar d procedures developed in these laboratories. Compounds 14 and 19 were then further converted to the target phosphonates 1b and 2b by modifi cation of literature procedures. The phosphonate 1b was 40-fold more c ytotoxic to HEp-2 cells than its parent, CDG, presumably after convers ion to the diphosphoryl phosphonate.