Forming spirocyclohexadienone-oxocarbenium cation species in the biomimetic synthesis of amomols

J Org Chem. 2011 Mar 4;76(5):1409-17. doi: 10.1021/jo102414s. Epub 2011 Jan 21.

Abstract

The oxidation of appropriate 2-(4-hydroxyphenyl)ethyl ketones gives direct access to amomols by means of the formation of a transient spirocyclohexadienone-oxocarbenium ion that is intermolecularly intercepted by an alcohol. Furthermore, homochiral amomols and other new analogues were synthesized for the first time and were biologically evaluated on Plasmodium falciparum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomimetics*
  • Cations / chemistry
  • Cations / metabolism
  • Cyclohexanes / chemistry*
  • Cyclohexanes / metabolism
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Furans / metabolism
  • Ketones / chemistry*
  • Ketones / metabolism
  • Molecular Structure
  • Oxidation-Reduction
  • Plasmodium falciparum / chemistry
  • Plasmodium falciparum / metabolism
  • Spiro Compounds / chemistry*
  • Spiro Compounds / metabolism
  • Stereoisomerism

Substances

  • Cations
  • Cyclohexanes
  • Furans
  • Ketones
  • Spiro Compounds