Convenient syntheses of biogenic aldehydes, 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde

Bioorg Chem. 2003 Apr;31(2):191-7. doi: 10.1016/S0045-2068(03)00019-1.

Abstract

The title compounds were prepared from a common precursor, a bis-THP-protected dihydroxyphenylacetic acid methyl ester. Key steps are the introduction of the alpha-hydroxyl group by Davis oxaziridine reagent and formation of the aldehydes by DIBALH ester reduction.

MeSH terms

  • 3,4-Dihydroxyphenylacetic Acid / analogs & derivatives*
  • 3,4-Dihydroxyphenylacetic Acid / chemical synthesis*
  • 3,4-Dihydroxyphenylacetic Acid / chemistry
  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Catechols
  • Hydrolysis
  • Hydroxyl Radical / chemistry
  • Indicators and Reagents

Substances

  • Aldehydes
  • Catechols
  • Indicators and Reagents
  • 3,4-Dihydroxyphenylacetic Acid
  • 3,4-dihydroxyphenylglycolaldehyde
  • Hydroxyl Radical
  • 3,4-dihydroxyphenylacetaldehyde