The potential of carbocyclic nucleosides for the treatment of AIDS: synthesis of carbocyclic 6′-fluoro-2′,3′-dideoxythymidine

Abstract

The carbocyclic nucleoside 4 and the corresponding triphosphate 5 were prepared from cyclopent-2-enylmethanol 6 in 8 and 10 steps respectively. The key step in the synthesis is the reaction of the azido alcohol 9 with diethylaminosulphur trifluoride: participation of the azido group led to the formation of the isomeric fluorides 10 and 11(ratio ca. 2:1). The triphosphate 5 was found to be a poor inhibitor of HIV-coded reverse transcriptase.