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Preparation of intermediates for copro porphyrin synthesis


, : Preparation of intermediates for copro porphyrin synthesis. Journal of Organic Chemistry 44(6): 973-977

The synthesis of dipyrrylmethanes necessary for the synthesis of coproporphyrins I-IV (1-4) is described. The synthesis of the former was designed so as to avoid isomeric mixtures to obtain pure samples of the latter. The asymmetric dibenzyl-3,4'-bis(.beta.-ethoxycarbonylethyl)-4,3'-dimethyl-5,5'-dipyrrylmethane and the symmetric dibenzyl 3,3'-dimethyl-4,4'-bis(.beta.-ethoxycarbonylethyl)-5,5'-dipyrrylmethanedicarboxylate were obtained. Hydrogenolysis of the dibenzyloxycarbonyl groups and condensation of the 5,5'-dicarboxydipyrrylmethanes with a 5,5'-diformyldipyrrylmethane gave coproporphyrins III and IV. Conversion of tert-butyl 3,4'-dimethyl-4,3'-bis(.beta.-ethoxycarbonylethyl)-5'-(benzyloxycarbonyl)-5-dipyrrylmethanecarboxylate into a (tert-butyloxycarbonyl)-5'-formyldipyrrylmethane was followed by treatment of the latter with HBr. By a self-condensation of the resulting product, coproporphyrin I was obtained in good yield.

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