SYNTHESIS OF CARBOCYCLIC 2',3'-DIDEOXY-2'-FLUORO-3'-C-HYDROXYMETHYL NUCLEOSIDE ANALOGS AS POTENTIAL INHIBITORS OF HIV AND HSV

The synthesis of four isomerically pure fluoro-carbocyclic adenosine a nd guanosine analogues is described. The 3S,4S-bis(t-butyldiphenylsily loxymethyl) derivatives 22, 23, 24 and 25 synthesised from enantiomeri cally pure -bis(t-butyldiphenylsilyloxymethyl)-cyclopentanone (18), we re coupled with chloropurines using the Mitsunobu procedure to give 10 , 11, 12, 14 and 16 or converted to their corresponding 1-amino deriva tives, from which the fluoro-carbocyclic guanosine analogues 13, 15 an d 17 were prepared. Compounds 10-17 were evaluated as potential anti-v iral agents but were found to be inactive. (C) 1997, Elsevier Science Ltd.