Concise and stereospecific synthesis of novel bicyclic dideoxynucleosides as potential antiviral agents
A novel class of dideoxynucleosides containing a bicyclic sugar moiety, structurally related to the natural griseolic acids, was synthesized starting from the stereochemically defined compound, 1,4:3,6-dianhydro-D-glucitol. The key intermediate in the synthesis was a [3.3.0] fused bicyclic glycal. Glycosylation of this compound with nucleobase proceeded both regiospecifically and stereospecifically in the presence of an auxiliary agent, N-iodosuccinamide. Changes in stereochemistry during the synthesis was monitored by optical rotation data and confirmed by both 1D and 2D NMR experiments. The synthetic approach described possesses general usefulness.
Chao, Qi, Jianzhong Zhang, Lea Pickering, Tamera S. Jahnke, and Vasu Nair. "Concise and stereospecific synthesis of novel bicyclic dideoxynucleosides as potential antiviral agents." Tetrahedron 54, no. 13 (1998): 3113-3124.