C-glycosyl juglone in angucycline synthesis: Total synthesis of galtamycinone, common aglycon of C-glycosyl naphthacenequinone-type angucyclines

Article abstract of DOI:10.1016/S0040-4020(97)01034-X

A two-step access to C-glycosyl juglones, 16 and 17, useful intermediates toward the angucyclines, either benz[a]anthraquinone- type or naphthacenequinone-type, has been developed based on (1) the O→C-glycoside rearrangement and (2) the regioselective cycloaddition of α-alkoxybenzyne and α-oxyfuran. The first total synthesis of galtamycinone (2), the common aglycon of naphthacenequinone-type angucyclines, has been achieved by utilizing 17 as the key intermediate.