Synthesis of neplanocin F analogues as potential antiviral agents

Neplanocin F is a natural carbocyclic nucleoside. Herein, we describe the synthesis and antiviral activity of (+/-)-5'-deoxyneplanocin F analogues. The key intermediate 4, synthesized from the commercially available (+/-)-2-azabicyclo[2.2.1]-hept-5-en-3-one (ABH), was utilized to prepare the target nucleosides. Among the target compounds, 5'-deoxyneplanocin F adenine exhibited moderate anti-HIV activity in human lymphocytes without any marked cytotoxicity. (c) 2006 Elsevier Ltd. All rights reserved.