Synthesis of d- and l-apio nucleoside analogues with 2′-hydroxyl group as potential anti-HIV agents Original Research Article

The present work describes the asymmetric synthesis of d- and l-apio-2′,3′-dideoxynucleoside analogues, 4 and 5 with 2′-hydroxyl group via a common intermediate 9, starting from d-galactose. Stereoselective dihydroxylation and deoxygenation through radical inversion were successfully employed to synthesize the key intermediate 12 with d-apio structure, while stereoselecetive hydroboration-oxidation was used for the synthesis of another key intermediate 18 with l-apio structure.