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Keywords:

  • alkaloid;
  • annulation;
  • natural products;
  • pyrones;
  • quinone methides
Thumbnail image of graphical abstract

Odd Couple: A method for the synthesis of alkaloid-pyrones using a novel pyrone annulation of β-carbolines and indoles with 3-siloxy-4-pyrones is reported. The approach has enabled synthesis of the unusual alkaloid-pyrone pleiomaltinine from the plant-derived indole-alkaloid pleiocarpamine (see Scheme; TBS= tert-butyldimethylsilyl).