Synthesis of Coumestrol and Aureol

J Nat Prod. 2016 Oct 28;79(10):2749-2753. doi: 10.1021/acs.jnatprod.6b00510. Epub 2016 Oct 5.

Abstract

A total synthesis of coumestrol (1) and aureol (2) is described. The Perkin condensation of 2-bromo-4-hydroxylphenylacetic acid (6) and o-hydroxybenzaldehydes (7) gave the corresponding 2'-bromo-3-arylcoumarins (9). A copper-catalyzed consecutive hydroxylation and aerobic oxidative coupling of 9 under microwave conditions facilitated the total synthesis of 1 and 2, respectively, with spectroscopic data highly similar to those of natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper / chemistry
  • Coumarins / chemistry
  • Coumestrol / chemical synthesis*
  • Coumestrol / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry

Substances

  • Coumarins
  • Sesquiterpenes
  • aureol
  • Copper
  • coumestan
  • Coumestrol