Concise syntheses of meridianins and meriolins using a catalytic domino amino-palladation reaction

Org Lett. 2014 Feb 7;16(3):708-11. doi: 10.1021/ol403390m. Epub 2014 Jan 17.

Abstract

A synthesis of natural and synthetic members of the meridianin family of kinase inhibitory natural products has been developed. The sequence utilizes a variation of the Cacchi palladium-catalyzed domino reaction to efficiently construct the heterocyclic framework of the meridianins and meriolins from monocyclic precursors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Catalysis
  • Heterocyclic Compounds, 1-Ring / chemical synthesis*
  • Heterocyclic Compounds, 1-Ring / chemistry*
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry*
  • Stereoisomerism

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • Heterocyclic Compounds, 1-Ring
  • Indole Alkaloids
  • Pyrimidines
  • meridianin A
  • meriolin 3
  • Palladium