Abstract
Several new polychlorinated imidazo[1,2-a]pyridine C-nucleosides have been prepared. Lithiated imidazo[1,2-a]pyridines were condensed with protected ribonolactones, trapped as 1‘-acetoxy derivatives, and these 1‘-acetoxy derivatives were reductively deacetoxylated and deprotected to give C-nucleosides. Long-range proton−carbon decoupling experiments were used to determine the actual site of ribosylation and established that the ribose moiety was unexpectedly attached to the C5 position of the imidazo[1,2-a]pyridines. This method has provided C-nucleosides, such as 2,6-dichloro-5-(β-d-ribofuranosyl)imidazo[1,2-a]pyridine and 2,6,7-trichloro-5-(β-d-ribofuranosyl)imidazo[1,2-a]pyridine and the corresponding α-products.
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