Open AccessTotal Synthesis of Hematoporphyrin and Protoporphyrin; a Conceptually New Approach
Author(s) -
Pierre Martin,
Markus Müller,
Dietmar Flubacher,
Andreas Boudier,
Dirk Spielvogel
Publication year - 2013
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2013.204
Subject(s) - porphyrin , hematoporphyrin , protoporphyrin ix , protoporphyrin , oxidizing agent , chemistry , combinatorial chemistry , condensation , salt (chemistry) , organic chemistry , photodynamic therapy , meteorology , physics
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.