Total Synthesis of Hematoporphyrin and Protoporphyrin; a Conceptually New Approach

Authors

  • Pierre Martin Solvias AG Römerpark 2, CH-4303 Kaiseraugst, Switzerland. pierre.martin@solvias.com
  • Markus Müller Solvias AG Römerpark 2, CH-4303 Kaiseraugst, Switzerland
  • Dietmar Flubacher Solvias AG Römerpark 2, CH-4303 Kaiseraugst, Switzerland
  • Andreas Boudier Solvias AG Römerpark 2, CH-4303 Kaiseraugst, Switzerland
  • Dirk Spielvogel Solvias AG Römerpark 2, CH-4303 Kaiseraugst, Switzerland

DOI:

https://doi.org/10.2533/chimia.2013.204

Keywords:

Development & scale-up, Novel porphyrin cyclization method, Process research, Protoporphyrin ix, Total synthesis

Abstract

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.

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Published

2013-04-24