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A Benzyne Insertion Approach to Hetisine-Type Diterpenoid Alkaloids: Synthesis of Cossonidine (Davisine).

  • Author(s): Kou, Kevin GM;
  • Pflueger, Jason J;
  • Kiho, Toshihiro;
  • Morrill, Louis C;
  • Fisher, Ethan L;
  • Clagg, Kyle;
  • Lebold, Terry P;
  • Kisunzu, Jessica K;
  • Sarpong, Richmond
  • et al.
Abstract

The hetisine-type natural products exhibit one of the most complex carbon skeletons within the diterpenoid alkaloid family. The use of network analysis has enabled a synthesis strategy to access alkaloids in this class with hydroxylation on the A-ring. Key transformations include a benzyne acyl-alkylation to construct a key fused 6-7-6 tricycle, a chemoselective nitrile reduction, and sequential C-N bond formations using a reductive cyclization and a photochemical hydroamination to construct an embedded azabicycle. Our strategy should enable access to myriad natural and unnatural products within the hetisine-type.

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