Опубликована: Май 29, 2024

We describe the first total synthesis of unusual cyclopropane-containing indole alkaloid (–)-rauvomine B via a strategy centered upon intramolecular cyclopropanation tetracyclic N-sulfonyl triazole. Preparation this precursor evolved through two generations synthesis, with ultimately successful route involving palladium-catalyzed stereospecific allylic amination, cis-selective Pictet–Spengler reaction, and ring-closing metathesis as important bond-forming reactions. The key step was found to be highly dependent on structure conformational strain indoloquinolizidine triazole precursor, origins which are explored computationally DFT studies. Overall, our proceeds in 11 steps 2.4% yield from commercial materials.

Язык: Английский