Synthesis of a potent antimalarial amphilectene

J Am Chem Soc. 2012 Dec 5;134(48):19604-6. doi: 10.1021/ja310129b. Epub 2012 Nov 15.

Abstract

7-Isocyano-11(20),14-epiamphilectadiene, the most potent of antimalarial amphilectenes, is synthesized in seven steps from readily available materials. The synthesis is enabled by a new dendrimeric triene (Danishefsky [3]-dendralene) and a new method for stereo- and chemoselective isocyanation. This chemistry provides a useful entry into an underexplored yet promising family of antimalarial terpenoids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / chemical synthesis*
  • Antimalarials / pharmacology
  • Diterpenes / chemical synthesis*
  • Diterpenes / pharmacology
  • Fibroblasts / drug effects*
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Plasmodium falciparum / drug effects*

Substances

  • 7-isocyano-11(20),14-epiamphilectadiene
  • Antimalarials
  • Diterpenes