Angiogenesis inhibitor epoxyquinol a: total synthesis and inhibition of transcription factor NF-kappaB

Org Lett. 2002 Sep 19;4(19):3267-70. doi: 10.1021/ol026513n.

Abstract

[reaction: see text] The asymmetric synthesis of the natural product (+)-epoxyquinol A (1) and related epoxyquinoid dimers, employing a cascade oxidation/electrocyclization/Diels-Alder dimerization sequence, is reported. In addition, we show that 1 and related molecules inhibit activation of the transcription factor NF-kappaB.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemical synthesis*
  • Angiogenesis Inhibitors / chemistry
  • Crystallography, X-Ray
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Hydroquinones / chemical synthesis*
  • Hydroquinones / chemistry
  • Molecular Conformation
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors*
  • NF-kappa B / metabolism

Substances

  • Angiogenesis Inhibitors
  • Epoxy Compounds
  • Hydroquinones
  • NF-kappa B
  • epoxyquinol A