First synthesis of 10 alpha-(trifluoromethyl)deoxoartemisinin

Org Lett. 2002 Mar 7;4(5):757-9. doi: 10.1021/ol017227z.

Abstract

[reaction: see text] A novel, nonacetal (trifluoromethyl)deoxoartemisinin was prepared with good stereoselectivity. This compound was obtained by debromination of the 10 alpha-CF3-10-bromodeoxoartemisinin in the presence of tributyltin hydride at reflux in toluene without alteration of the endoperoxide bridge. It presented a reasonable antimalarial activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / pharmacology
  • Artemisia / chemistry
  • Artemisinins / chemical synthesis*
  • Artemisinins / pharmacology
  • Drug Resistance
  • Halogens / chemistry
  • Inhibitory Concentration 50
  • Plasmodium falciparum / drug effects
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / pharmacology
  • Stereoisomerism

Substances

  • 10-(trifluoromethyl)deoxoartemisinin
  • Antimalarials
  • Artemisinins
  • Halogens
  • Sesquiterpenes
  • artemisinin