Synthesis 2024; 56(16): 2549-2557
DOI: 10.1055/s-0043-1775368
paper

Synthesis of Methoxy Analogues of Coenzyme Q10 Metabolites from Parsley Seed Extracts via Baeyer–Villiger Rearrangement of Carbonyl-Substituted Polyalkoxybenzenes

Authors

  • Dmitry V. Demchuk

  • Olga I. Adaeva

  • Dmitry V. Tsyganov

  • Darina I. Nasyrova

  • Roman A. Dolotov

  • Еgor А. Muravsky

  • Alexander E. Varakutin

  • Alexander V. Samet

  • Victor V. Semenov


Russian Science Foundation Grant 24-23-00024.


Graphical Abstract

Preview

Abstract

Based on the parsley seed main component, apiol, efficient approach to polymethoxyquinone C3- and C4-acids was developed. The key step of this approach is Baeyer–Villiger rearrangement of carbonyl-substituted polyalkoxybenzenes derived from parsley seed extracts. These acids are the MeO-analogues of natural antioxidants – metabolites of ubiquinone and idebenone. Due to antioxidant properties, they are the potential therapeutic candidates for the treatment of mitochondrial dysfunction.

Supporting Information



Publikationsverlauf

Eingereicht: 20. Februar 2024

Angenommen nach Revision: 16. Mai 2024

Artikel online veröffentlicht:
18. Juni 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany