Development of an iron(II)-catalyzed aerobic catechol cleavage and biomimetic synthesis of betanidin

Nicolas Guimond, Peter Mayer, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

An aerobic iron(II)-catalyzed cleavage of catechols was developed. This reaction allows for the preparation of 2-methoxy-2H-pyrans that can be employed as versatile building blocks for synthesis. The utility of this biomimetic oxidative cleavage is featured in the synthesis of betanidin, a natural colorant with antioxidant properties. Cut and paste: An aerobic iron(II)-catalyzed oxidative cleavage of catechol was developed. This reaction allows the preparation of 2H-pyrans that can be employed as versatile building blocks for synthesis. The utility of this biomimetic cleavage is featured in the synthesis of betanidin, the aglycone of red beets' principal colorant and itself a valuable antioxidant (see scheme).

Original languageEnglish (US)
Pages (from-to)9519-9523
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number31
DOIs
StatePublished - Jul 28 2014

Keywords

  • aerobic oxidation
  • betalain
  • biomimetic synthesis
  • green chemistry
  • iron

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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