Syntheses of Derivatives of Protoporphyrin IX Bearing Deuteriated Methyls on the Propionate (C and D) Rings

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New syntheses of hemins that are regioselectively deuteriated in the 5- and 8-methyls (14) and the 8-methyl (31) are described. The 5,8-dilabeled porphyrin 3 was obtained via an acrylate porphyrin by conversion of deuteroporphyrin IX dimethyl ester (2) into the corresponding bis(acrylate) 5 using LDA, benzeneselenenyl bromide, and oxidative elimination. After base-catalyzed deuterium exchange, reduction of the acrylate to propionate, and vinylation, the required 5,8-dilabeled porphyrin was obtained. The 8-methyl-deuteriated compound 15 was obtained by total synthesis through a porphyrin 16 bearing an unsubstituted 7-position. By a mercuration/ palladium-olefin reaction, the vacant position was substituted with an acrylate, and following base-catalyzed exchange, hydrogenation, and construction of the 2- and 4-vinyls, the required product was obtained. These compounds, as the corresponding iron complexes (hemins), are of interest in connection with heme/apoprotein reconstitution studies and for characterization of structure/function relationships in heme proteins. © 1986, American Chemical Society. All rights reserved.

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Journal of Organic Chemistry

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