ABSTRACT
Synthesis and antiviral activity of several new 8-substituted carbocyclic analogs of D-2′,3′-dideoxyadenosine are described. The new 8-substituted analogs were synthesized via lithiation of carbocyclic 2′,3′-dideoxy adenosine followed by quenching with electrophiles. This methodology allows for a divergent synthesis of a variety of 8-substituted analogs from carbocyclic 2′,3′-dideoxyadenosine in high yields. 8-Methyl and 8-halogenated carbocyclic 2′,3′-dideoxyadenosine analogs showed 6–25 fold more activity against hepatitis B virus than the unsubstituted carbocyclic D-2′,3′-dideoxyadenosine.