Enantioselective Synthesis of Azamerone

J Am Chem Soc. 2019 Feb 20;141(7):2867-2871. doi: 10.1021/jacs.8b12566. Epub 2019 Feb 8.


A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of natural-product-relevant chiral organochlorides motivated the development of unique strategies for accessing these motifs in enantioenriched forms. The route features a novel enantioselective chloroetherification reaction, a Pd-catalyzed cross-coupling between a quinone diazide and a boronic hemiester, and a late-stage tetrazine [4+2]-cycloaddition/oxidation cascade.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Benzoquinones / chemistry
  • Boronic Acids / chemistry
  • Cycloaddition Reaction
  • Oxidation-Reduction
  • Stereoisomerism
  • Terpenes / chemical synthesis*


  • Benzoquinones
  • Boronic Acids
  • Terpenes
  • azamerone