SYNTHESIS OF BICARBOCYCLIC DIDEOXYNUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS

Two novel classes of bicarbocyclic dideoxynucleosides have been synthe sized for antiviral studies. The key intermediates, 9 and 23, synthesi zed in multiple steps from readily available monocyclic or bicyclic pr ecursors, were coupled with the desired heterocyclic bases to afford, after further elaboration, the corresponding bicarbocyclic dideoxynucl eosides. The structure and stereochemistry of the tosylate intermediat es and the target bicarbocyclic dideoxynucleosides were confirmed by e xtensive H-1 and C-13 NMR studies including COSY, NOESY, DEFT, and sel ective INEPT experiments. (C) 1997, Elsevier Science Ltd.