Synthesis of 3,3',5-trihydroxybiphenyl-2-carboxylic acid, a component of the bitterest natural product amarogentin and its coenzyme A and N-acetyl cysteamine thiol esters

J Nat Prod. 2000 Mar;63(3):371-4. doi: 10.1021/np990256m.

Abstract

3,3',5-Trihydroxybiphenyl-2-carboxylic acid (6), an ester component of the bitter-tasting natural products amarogentin and amaroswerin, was synthesized in six steps in 13.6% overall yield. Its N-acetyl cysteamine thiol ester (9) and its coenzyme A thiol ester (8), a likely biosynthetic precursor of the amarums, were also prepared.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coenzyme A / chemistry*
  • Cysteamine / analogs & derivatives*
  • Cysteamine / chemistry
  • Esters
  • Glucosides / chemistry*
  • Iridoids*
  • Molecular Structure
  • Pyrans / chemistry*
  • Spectrum Analysis

Substances

  • Esters
  • Glucosides
  • Iridoids
  • Pyrans
  • amarogentin
  • Cysteamine
  • Coenzyme A