An efficient and versatile strategy of general applicability towards apio and homologated apio pyrimidines has been delineated. The methodology shows tosylation followed by in situ cyclization and one pot oxidative cleavage and acetylation by Pb(OAc)4 as the key steps. The methodology has been applied to D-ribose and D-mannose derivatives to achieve asymmetric synthesis of apio and homologated apio pyrimidine nucleosides.
