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Keywords:

  • alkaloids;
  • natural products;
  • palladium;
  • paspalinine;
  • total synthesis
Thumbnail image of graphical abstract

Succinct and stereoselective: A high-yielding two-step indole ring installation comprising the Stille cross-coupling and a PdII-mediated oxidative heterocyclization was exploited in a concise total synthesis of paspalinine. The trans-anti-trans CDE fused ring system of the heptacyclic natural product was established highly stereoselectively through hydroxy-directed cyclopropanation and allylic selenoxide rearrangement.