Synthesis of 2’-Deoxy-2’-fluoro-L-arabinofuranosyl Imidazole Derivatives

The last few years have witnessed a revival of interest in analogues of nucleosides following the discoveries that several of such compounds exhibit powerful antiviral effects. Structural modifications of naturally occurring nucleosides often lead to the discovery of new agents displaying biological and chemotherapeutic activity. A greal deal of effort has been directed towards the modifications at the nucleobase1−3. An imidazole nucleoside, 5-amino imidazole-4-carboxamide riboside (AICA riboside), is known to be involved in the de novo biosynthesis of purine nucleotides. It is also produced in histidine biosynthesis and is associated with the histamine metabolism. The naturally occurring nucleoside antibiotic, bredinin (Figure 1), has been isolated from the culture of Eupenicillium brefeldianum and shown to possess immunosuppressive properties as well as other biological activities.