Versatile and expeditious synthesis of aurones via Au I-catalyzed cyclization

J Org Chem. 2008 Feb 15;73(4):1620-3. doi: 10.1021/jo702197b. Epub 2008 Jan 15.

Abstract

Aurones are conveniently formed in a three-step procedure including a goldI-catalyzed cyclization of 2-(1-hydroxyprop-2-ynyl)phenols as a highly regio- and stereoselective key step. A wide diversity of derivatives can be obtained starting from substituted salicylaldehydes. Synthesis of natural 4,6,3',4'-tetramethoxyaurone and structure revision of two natural products (dalmaisione D and 4'-chloroaurone) were achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / chemical synthesis*
  • Cyclization
  • Gold / chemistry*
  • Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Benzofurans
  • aurone
  • Gold