The preparation of porphyrin S-411 (dehydrocoproporphyrin) and harderoporphyrin from protoporphyrin IX

Abstract

Protoporphyrin IX dimethyl ester has been converted into the two 2,4-positional isomers bearing hydroxyethyl and methoxycarbonylvinyl side chains. The 4-(2-hydroxyethyl) group was extended to a methoxycarbonylethyl group to give the tetramethyl ester of porphyrin S-411 (2-methoxycarbonylvinyl-4-methoxycarbonylethyldeuteroporphyrin dimethyl ester). On the other hand reduction of the 4-methoxycarbonylvinyl to the corresponding methoxycarbonylethyl group and dehydration of the 2-(2-hydroxyethyl) to a vinyl side chain gave the trimethyl ester of harderoporphyrin (2-vinyl-4-methoxycarbonylethyldeuteroporphyrin dimethyl ester).