Protection-group-free semisyntheses of parthenolide and its cyclopropyl analogue

J Org Chem. 2013 Oct 18;78(20):10512-8. doi: 10.1021/jo401606q. Epub 2013 Sep 27.

Abstract

Parthenolide showed extensive bioactivities including selective eradication of AML stem cells. Herein we report protection-free semisyntheses of parthenolide and its cyclopropyl analogue (compound 10) from the abundant natural product costunolide with an overall yield of 55 and 60%, respectively. Compound 10 was more stable than parthenolide, and it maintained comparable activities against AML cell lines and AML stem cells. Therefore, compound 10 might be a superior small molecule than parthenolide as a tool for investigation of cancer stem cell biology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apoptosis
  • Cell Line, Tumor
  • Cyclopropanes / chemistry*
  • Humans
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry*

Substances

  • Cyclopropanes
  • Sesquiterpenes
  • parthenolide
  • costunolide