Login / Signup

En Route to D-Ring Inverted Phorbol Esters.

Sharon ChowTanja KrainzPaul V BernhardtCraig M Williams
Published in: Organic letters (2019)
Phorbol esters are long regarded as tumor promotors, due to protein kinase C (PKC) activation, but more recently higher oxidized natural derivatives have been shown to display antitumor activity. Given the synthetic difficulty, systematic non-natural systems are not readily available to further interrogate PKC binding. Herein reported is the concise construction of a considerably advanced intermediate toward D-ring inverted phorbol esters, enabled by a rhodium-catalyzed [4 + 3] cycloaddition involving a highly functionalized tetrahydrobenzofuran.
Keyphrases
  • protein kinase
  • mass spectrometry
  • binding protein
  • high resolution
  • molecularly imprinted
  • liquid chromatography
  • solid phase extraction