The Chemistry of Pyrrolic Compounds. LXV. Intramolecular Cyclization of Porphyrins With Acetic Acid Side Chains: Hydroxy Derivatives of Deoxophylloerythroaetioporphyrin (DPEP)

Abstract

The intramolecular cyclization of porphyrins substituted with an acetic acid side chain has been studied under a range of conditions but the yield of product bearing a fused five- membered ketonic ring system was disappointingly low. Deoxophylloerythroaetioporphyrin (DPEP) derivatives with hydroxy groups at either C 13′ or C 15′ have been prepared by reduction of the corresponding ketones. ¹H n.m.r . data for the latter alcohol matches well that reported for a porphyrin obtained from Marl Slate and which is probably derived from DPEP, by oxidation, during the extraction process.