Total Synthesis of Hematoporphyrin and Protoporphyrin: A Conceptually New Approach

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• 作者：Pierre Martin ; Markus Mueller ; Dietmar Flubacher ; Andreas Boudier ; Hans-Ulrich Blaser ; Dirk Spielvogel
• 刊名：Organic Process Research & Development
• 出版年：2010
• 出版时间：July 16, 2010
• 年：2010
• 卷：14
• 期：4
• 页码：799-804
• 全文大小：227K
• 年卷期：v.14,no.4(July 16, 2010)
• ISSN：1520-586X

文摘

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.