Title
New efficient total syntheses of derivatives of protoporphyrin‐IX bearing deuteriated methyl groups
Document Type
Article
Publication Date
1-1-1983
Abstract
New total syntheses of hemins which are regioselectively deuteriated in the 1,5 (2), 5 (3) or 8 (4) methyl groups are described. Syntheses of hemins 2 and 3 follow the progression from pyrromethane 12 to t‐butyl tripyrrene‐carboxylate hydrobromide (17 and 30) and then to a,c‐biladiene dihydrobromide (19 and 31), but for reasons of economy in use of labeled monopyrroles, the o,c‐biladiene dihydrobromide 40 for hemin 4 is approached in an initially “clockwise” manner by synthesis of a benzyl tripyrrene‐carboxylate hydrobromide 37 from the pyrromethane 5. Cyclization of the a,c‐biladienes (19, 31, and 40) was accomplished by brief heating in dimethylformamide in the presence of copper(II) chloride. Copyright © 1983 Journal of Heterocyclic Chemistry
Publication Source (Journal or Book title)
Journal of Heterocyclic Chemistry
First Page
1383
Last Page
1388
Recommended Citation
Smith, K., & Pandey, R. (1983). New efficient total syntheses of derivatives of protoporphyrin‐IX bearing deuteriated methyl groups. Journal of Heterocyclic Chemistry, 20 (5), 1383-1388. https://doi.org/10.1002/jhet.5570200543