A short high yielding synthesis of the potent anti-varicella-zoster virus (VZV) carbocyclic nucleoside analog carba-BVDU I [R = CH:CHBr-(E), R1 = H] starting from aminodiol II is described.Reaction of II with the acyl carbamate, EtOCH:CEtCONHCO2Et, and subsequent ring closure under acidic conditions afforded 5-ethyl-2'-deoxy-4'a-carbauridine (I; R = Et, R1 = H).In situ acetylation of I ( R = Et, R1 = H) afforded 3',5'-di-O-acetyl-5-ethyl-2'-deoxy-4'a-carbauridine (I; R = Et, R1 = Ac) in 78% overall yield from II.Radical bromination of I (R = Et, R1 = Ac) with either bromine or NBS and subsequent treatment with triethylamine gave an efficient conversion to 3',5'-di-O-acetyl-5-(E)-(2-bromovinyl)-2'-deoxy-4'a-carbauridine [I; R = CH:CHBr-(E), R1 = Ac].Deacetylation of I [R = CH:CHBr-(E),R1 = Ac] afforded I [R = CH:CHBr-(E), R1 = H] in an overall 45-33% yield from II.