Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry

J Org Chem. 2013 Oct 4;78(19):9876-82. doi: 10.1021/jo401583q. Epub 2013 Sep 23.

Abstract

The title natural products (1 and 2, respectively) have been synthesized by Au(I)-catalyzed intramolecular hydroarylation (IMHA) of the relevant aryl propiolate esters (e.g., 13), which were themselves formed by reaction of the corresponding phenols with either 3-(trimethylsilyl)propiolic acid or propiolic acid and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride or dicyclohexylcarbodiimide. (±)-Purpurasol (3) was readily derived from fraxetin (2) by established procedures.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Catalysis
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Gold
  • Hydroxylation
  • Methoxsalen / analogs & derivatives*
  • Methoxsalen / chemical synthesis
  • Methoxsalen / chemistry
  • Molecular Structure
  • Organic Chemistry Phenomena

Substances

  • Biological Products
  • Coumarins
  • Gold
  • coumarin
  • fraxetin
  • pimpinellin
  • Methoxsalen