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Keywords:

  • alkaloids;
  • annulation;
  • carbazoles;
  • methoxypropadienes;
  • natural products;
  • synthetic methods
Thumbnail image of graphical abstract

Accessible alkaloids: Naturally occurring carbazole alkaloids, such as clauszoline-K, -L, -M, and -N, 3-formyl-7-hydroxycarbazole, and siamenol, were synthesized through a gold-catalyzed cyclization reaction of 1-(indol-2-yl)-2-methoxy-2,3-allenols, which are readily available from indolecarbaldehydes and methoxypropadiene (see scheme; R1=Me, carboxylic acid/ester, or aldehyde; R2=prenyl or H; R3=H or Me). The reaction demonstrates atom economy, high selectivity, and high yields, mostly with catalytic reactions.