Synthesis of 8-aryl-substituted coumarins based on ring-closing metathesis and Suzuki-Miyaura coupling: synthesis of a furyl coumarin natural product from Galipea panamensis

J Org Chem. 2012 Mar 2;77(5):2360-7. doi: 10.1021/jo2026564. Epub 2012 Feb 10.

Abstract

The synthesis of 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one, a natural product with antileishmanial activity recently isolated from the plant Galipea panamensis, is described. The key step is a Suzuki-Miyaura coupling of a furan-3-boronic acid and an 8-halocoumarin, which is advantageously synthesized using a ring-closing metathesis reaction. Several non-natural analogues are also available along these lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Cyclization
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Rutaceae / chemistry*
  • Stereoisomerism

Substances

  • Biological Products
  • Coumarins
  • Organometallic Compounds