Abstract A short high yielding synthesis of the potent anti-varicella-zoster virus (VZV) carbocyclic nucleoside analogue carba-BVDU 1 starting from aminodiol 2 is described. Reaction of 2 with acyl carbamate 3 and subsequent ring closure under acidic conditions afforded 5-ethyl-2′-deoxy-4′ a-carbauridine 5. In situ acetylation of 5 afforded 3′, 5′-di- O-acetyl-5-ethyl-2′-deoxy-4′ a-carbauridine 6 in 78% overall yield from 2. Radical ...
