An efficient chloro-deamination procedure, application to the synthesis of advanced vancomycin C-O-D-O-E ring

An efficient chloro-deamination procedure was developed and a remarkable deuterium isotope effect indicating a radical mechanism was documented. Key to success was the coexistence of a reductant (CuCl) and a ligand-transfer agent (CuCl2) in the reaction medium employing CD3CN as co-solvent of CCl4. The procedure was applied to the synthesis of advanced vancomycin models. [on SciFinder (R)]