Continuous Flow Photocatalysis Enhanced Using an Aluminum Mirror: Rapid and Selective Synthesis of 2’-Deoxy and 2’,3’-Dideoxynucleosides

Chemical Communications 48, 7444-7446, DOI: 10.1039/C2CC33356B

Many deoxynucleosides have potent effects against viruses and tumors. Several have been approved as antiviral and/or anti-cancer drugs, including zidovudine, stavudine, trifluridine, idoxuridine, cladribine and didanosine (Fig. 1). Extraction from natural sources and fermentation processes provide only a limited number of naturally occurring 2′-deoxynucleosides; therefore, chemical approaches for the general synthesis of deoxynucleosides are highly desired.2 A common strategy is the direct SN2 reaction between a 1-chloro-2-deoxyribose derivative and a metalated or silylated nitrogenous base. Drawbacks of this strategy are the costs and stereochemical lability of 1-chloro sugars. Furthermore, the substitution reaction tends to generate a mixture of anomers that are difficult to separate"