Synthesis of aristeromycin analogs.

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Abstract
Reaction of aristeromycin (I) with acetyl bromide in acetonitrile, followed by treatment with hydrobromic acid afforded 3'β-bromo-3'-deoxyaristeromycin hydrobromide (V) and 2'β-bromo-2'-deoxyaristeromycin hydrobromide (VI). Catalytic reduction of V and VI with palladium on charcoal gave 3'-deoxyaristeromycin (X) and 2'-deoxyaristeromycin (XI), respectively. Treatment of V with sodium alkoxide yielded 2', 3'-anhydroaristeromycin (IV). Two carbocyclic analogs (XII and XV) of inosine and 6-mercaptopurine ribonucleoside, 8-bromoaristeromycin (XVI) and 8-hydroxyaristeromycin (XVII) were also prepared.