Synthetic and biosynthetic studies of porphyrins. Part 11. The synthesis of meso oxygenated protoporphyrins

Abstract

Treatment of protoporphyrin IX dimethyl ester (12) with benzoyl peroxide affords a mixture of the four isomeric meso-benzoyloxy derivatives (13). These have been separated by h.p.l.c. and distinguished from each other by hydrolysis to the corresponding oxophlorins (oxyporphyrins), insertion of iron to form the oxyhaems (3), and oxidation by molecular oxygen to the corresponding biliverdins (7).