Photoinduced electron-transfer α-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-d-arabino-hexono-1,4-lactone Original Research Article

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-lactones were efficiently obtained.