The chemistry of pyrrolic compounds. XXIV. The synthesis of an isomer of coproporphyrin and related compounds

Abstract

Using a bilene-b intermediate the acetylporphyrin (1e) has been prepared. This porphyrin has been converted into the corresponding β- free (1i), hydroxyethyl (1f), vinyl (1h), and ethyl (1g) derivatives. The latter porphyrin (1g) is an isomer of coproporphyrin. Porphyrins (1g) and (1f) have been compared with the series of compounds isolated from patients suffering from symptomatic cutaneous hepatic porphyria. The synthetic porphyrins were not identical with material isolated from porphyric patients.