Total Synthesis of Hematoporphyrin and Protoporphyrin: A Conceptually New Approach

✍ Scribed by Martin, Pierre; Mueller, Markus; Flubacher, Dietmar; Boudier, Andreas; Blaser, Hans-Ulrich; Spielvogel, Dirk

• Book ID: 121840141
• Publisher: American Chemical Society
• Year: 2010
• Tongue: English
• Weight: 286 KB
• Volume: 14
• Category: Article
• ISSN: 1083-6160
• DOI: 10.1021/op100036c

✦ Synopsis

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.