Synthesis of carbocyclic 2',3'-dideoxy-2'-fluoro-3'-C-hydroxymethyl nucleoside analogues as potential inhibitors of HIV and HSV

Article abstract of DOI:10.1016/S0040-4020(96)01103-9

The synthesis of four isomerically pure fluoro-carbocyclic adenosine and guanosine analogues is described. The 3S,4S-bis(t-butyldiphenylsilyloxymethyl)-2-fluoropentan- 1-ol derivatives 22, 23, 24 and 25 synthesised from enantiomerically pure 3S,4S-bis(t-butyldiphenylsilyloxymethyl)-cyclopentanone (18), were coupled with chloropurines using the Mitsunobu procedure to give 10, 11, 12, 14 and 16 or converted to their corresponding 1-amino derivatives, from which the fluoro-carbocyclic guanosine analogues 13, 15 and 17 were prepared. Compounds 10-17 were evaluated as potential anti-viral agents but were found to be inactive.