Total synthesis and biological evaluation of verticipyrone and analogues

Org Lett. 2007 Jan 4;9(1):65-7. doi: 10.1021/ol0626140.

Abstract

[reaction: see text] Total synthesis of verticipyrone, a novel NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach using novel "Reverse Julia olefination" method. During total synthetic studies, we also prepared and evaluated several synthetic verticipyrone analogues, some of which exhibited more potent antiparasitic activity than the natural verticipyrone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis
  • Aldehydes / chemistry
  • Alkenes / chemistry*
  • Molecular Structure
  • Oxidoreductases Acting on CH-CH Group Donors / antagonists & inhibitors
  • Oxidoreductases Acting on CH-CH Group Donors / metabolism
  • Pyrones / chemical synthesis
  • Pyrones / chemistry*
  • Pyrones / pharmacology*
  • Structure-Activity Relationship

Substances

  • Aldehydes
  • Alkenes
  • Pyrones
  • verticipyrone
  • Oxidoreductases Acting on CH-CH Group Donors
  • fumarate reductase (NADH)