Summary
On treating xanthobilirubic acid methyl ester with bromine in methanol, a red bile pigment, which was assigned the hitherto unknown 16,24-dehydrobiladiene-ab constitution, is obtained in 20% yield. In addition, the corresponding mesobiliverdin-XIIIα, mesobilirubin-XIIIα, 14-formyl-tripyrrinone, and two diastereomeric 15,16-dimethoxybiladienes-ab could be isolated from the reaction mixture. The mechanistic aspects of this reaction are discussed.
Zusammenfassung
Der Umsatz von Xanthobilirubinsäuremethylester mit Brom in Methanol ergibt in 20-prozentiger Ausbeute ein rotes Pigment, für das die bislang nicht bekannte 16,24-Dehydrobiladien-ab-Konstitution abgeleitet wurde. Darüber hinaus konnte das entsprechende Mesobiliverdin-XIIIα, Mesobilirubin-XIIIα, 14-Formyltripyrrinon, und zwei diastereomere 15,16-Dimethoxybiladiene-ab aus der Reaktionsmischung isoliert werden. Die mechanistischen Aspekte dieser Reaktion werden diskutiert.
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Ma, J.S., Chen, Q.Q., Wang, C.Q. et al. A novel 16,24-dehydrobiladiene-ab system: The reaction of xanthobilirubic acid methyl ester with bromine. Monatsh Chem 126, 201–209 (1995). https://doi.org/10.1007/BF00812248
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DOI: https://doi.org/10.1007/BF00812248