Total syntheses of derivatives of protoporphyrin IX regioselectively labeled with carbon-13 in the methyls

KM Smith, EM Fujinari, RK Pandey…

Index: Smith, Kevin M.; Fujinari, Eugene M.; Pandey, Ravindra K.; Tabba, Hani D. Journal of Organic Chemistry, 1986 , vol. 51, # 24 p. 4667 - 4676

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Citation Number: 13

Abstract

Total syntheses, from monopyrroles via tripyrrenes and apbiladienes, of the four isomers 2-5 of protoporphyrin IX dimethyl ester in which the 1-, 3-, 5-, and 8-methyl groups are individually and regioselectively enriched with carbon-13 are described. The source of labeled carbon was 90% carbon-13-enriched paraformaldehyde, and methyls were inserted at the monopyrrole stage by reductive C-alkylation. The carbon-13-labeled porphyrins, as ...