Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement

Research output: Contribution to journalArticlepeer-review

Abstract

Prunetin (4',5-dihydroxy-7-methoxyisoflavone) was semisynthesized in 8 steps from readily available naringenin in 26% total yield. The key reaction was chemoenzymatic sequential deacetylation to 6'-acetoxy-2',4″-dihydroxy-4'-methoxychalcone, the in situ-formed precursor for thallium(III) nitrate-mediated oxidative rearrangement.

Original languageEnglish
Pages (from-to)143-147
Number of pages5
JournalBioscience, Biotechnology, and Biochemistry
Volume85
Issue number1
DOIs
Publication statusPublished - 2021 Jan 7

Keywords

  • O-methylated isoflavone
  • chalcone
  • deacetylation
  • naringenin
  • oxidative rearrangement

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement'. Together they form a unique fingerprint.

Cite this