Synthetic approach to hypoxyxylerone, novel inhibitor of topoisomerase I

Org Lett. 2002 Sep 5;4(18):3139-42. doi: 10.1021/ol026454d.

Abstract

[reaction: see text] A potential route to the topoisomerase I inhibitor hypoxyxylerone is demonstrated by a highly convergent synthesis of the penta(O-methyl) derivative. The key step in the approach is an anionic homo-Fries rearrangement, little used to date in natural product synthesis and employed here for the first time with a dinaphthalenic substrate, to access the pentacyclic system of hypoxyxylerone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Enzyme Inhibitors / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Mycotoxins / chemical synthesis
  • Topoisomerase I Inhibitors*
  • Xanthenes / chemical synthesis

Substances

  • Enzyme Inhibitors
  • Heterocyclic Compounds, 4 or More Rings
  • Mycotoxins
  • Topoisomerase I Inhibitors
  • Xanthenes
  • dibenzoxanthenes
  • hypoxyxylerone