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

Biosci Biotechnol Biochem. 2021 Jan 7;85(1):143-147. doi: 10.1093/bbb/zbaa021.

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.

Keywords: O-methylated isoflavone; chalcone; deacetylation; naringenin; oxidative rearrangement.

MeSH terms

  • Acetylation
  • Chalcone / chemistry*
  • Chemistry Techniques, Synthetic
  • Flavanones / chemistry*
  • Isoflavones / chemical synthesis*
  • Isoflavones / chemistry*
  • Methylation
  • Oxidation-Reduction
  • Oxygen / chemistry*

Substances

  • Flavanones
  • Isoflavones
  • prunetin
  • Chalcone
  • naringenin
  • Oxygen