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Total Synthesis of Hematoporphyrin and Protoporphyrin: A Conceptually New Approach

The total synthesis of protoporphyrin IX and its disodium salt using a new alternative method to the classical MacDonald condensation is reported. The key step is the reaction of the new unsymmetrical diiodo dipyrrylmethane 1 with the known dipyrrylmethane 2. Coupling of the two fragments leads dire...

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Bibliographic Details
Published in:Organic process research & development 2010-07, Vol.14 (4), p.799-804
Main Authors: Martin, Pierre, Mueller, Markus, Flubacher, Dietmar, Boudier, Andreas, Blaser, Hans-Ulrich, Spielvogel, Dirk
Format: Article
Language:English
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Summary:The total synthesis of protoporphyrin IX and its disodium salt using a new alternative method to the classical MacDonald condensation is reported. The key step is the reaction of the new unsymmetrical diiodo dipyrrylmethane 1 with the known dipyrrylmethane 2. Coupling of the two fragments leads directly to porphyrin 3 without the need of an oxidizing agent. The new methodology is well suited for the synthesis of protoporphyrin IX derivatives on a multi 100 g scale in good quality without the need for chromatography. Furthermore, these preparations are completely free of any contaminant of animal origin, which represents a real improvement in the manufacturing of protoporphyrin IX derivatives.
ISSN:1083-6160
1520-586X
DOI:10.1021/op100036c