Photoinduced electron-transfer alpha-deoxygenation of aldonolactones.Efficient synthesis of 2-deoxy-D-arabino hexono-1,4-lactone

摘要

A photoinduced electron-transfer(PET)reaction was used for the deoxygenation at C-2 of aldonolactones derivatized as 2-O-[3-(trifluoromethyl)benzoyl] or benzoyl esters.By irradiation of different D-galactono-and D-glucono-1,4-derivatives,with a 450 W lamp,using 9-methylcarbazole as photosensitizer,the corresponding 2-deoxy-D-lyxo-and 2-deoxy-D-arabino-hexono-1,4-lac-tones were efficiently obtained.