Copper(I)-mediated and microwave-assisted C(aryl)-O(carboxylic) coupling: synthesis of benzopyranones and isolamellarin alkaloids

J Org Chem. 2007 Nov 23;72(24):9379-82. doi: 10.1021/jo701599g. Epub 2007 Nov 2.

Abstract

A simple and highly effective C-O(carboxylic) coupling reaction catalyzed by copper(I) salts has been developed to synthesize benzopyranones. The reaction of various 2-halobiarylcarboxylic acids was examined using microwave irradiation. A new class of pyrroloisoquinoline alkaloid, isolamellarin, was synthesized based on the annulation of dihydroisoquinoline with aryl pyruvates under basic condition and Cu-mediated/MW-assisted C-O(carboxylic) lactonization.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Antineoplastic Agents / chemical synthesis*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Coumarins / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Hydrocarbons, Cyclic / chemistry*
  • Microwaves*
  • Models, Chemical

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Carboxylic Acids
  • Coumarins
  • Heterocyclic Compounds, 4 or More Rings
  • Hydrocarbons, Cyclic
  • lamellarin alpha
  • Copper