Abstract
Intramolecular oxidative coupling of tryptamine incorporated amide was used to create the quaternary spiroin- doline carbon center of communesins, which enabled a short asymmetric synthesis of (-)-communesins A and B and F. The fused tetra-ring framework of Vincorine was established by an intramolecular oxidative coupling/condensative cyclization process, which was further advanced to (-)-vincorine in 5 steps. From a medicinal standpoint, such a cascade process pro- vides a highly diverse, efficient method for the construction of polycyclic spiroindoline scaffolds. Starting from easily accessi- ble tryptamine incorporated β-ketoamides and malonamides, polyclic spiroindolines and pyrroloindolines could be directly obtained by adopting the same cascade strategy. Keywords intramolecular oxidative coupling; indole alkaloids; total synthesis; polycyclic spiroindoline; pyrroloindoline
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