The potential for using carbocyclic nucleosides for the treatment of AIDS. Part 1. Preparation of some analogues for azidothymidine (AZT)

Abstract

The tricyclic compound 10 was converted into the fluoronorbornane 11 and the norbornanol 23 using fluoride ion and water respectively. The fluoro compound 11 was converted into the carbocyclic nucleosides 5 and 7 by a series of stereocontrolled reactions. Similarly the alcohol (23) furnished the nucleoside analogue 6. Compound 5 showed weak anti-HIV (Human Immunodeficiency Virus) activity and the corresponding triphosphate 27 inhibited HIV-reverse transcriptase to a small degree. The relatively weak antiviral activity of compounds 5–7 compared to compounds 1 and 2 can be ascribed to the different preferred conformations of the two sets of compounds.