Synthesis of novel 3′,4′-seco analogues of didehydro dideoxy nucleosides as potential antiviral agents

Abstract

Novel acyclo analogues ( 13, 14) of didehydro dideoxy adenosine (d4A) lacking C-3′C-4′ bond were synthesized as potential anti-HIV agents. The key step involves the bromination of unsaturated isomer 6 with NBS in mono protected ethylene glycol leading to 3′,4′-seco-2′-bromo-3′-hydroxy compound 11a. Activation of 3′-hydroxy group and reductive elimination of vicinal bromo tosylate gave 13 which on deprotection was converted into the target molecule 14.