Study toward an Asymmetric and Catalytic Synthesis of Koumine

@article{Maddaluno2019StudyTA,
  title={Study toward an Asymmetric and Catalytic Synthesis of Koumine},
  author={J. Maddaluno and D. Loya and M. D. Paolis},
  journal={Heterocycles},
  year={2019},
  volume={99},
  pages={1388}
}
A synthetic study of koumine, a natural product with a densely functionalized and inspiring heterocyclic skeleton, was conducted by exploring a strategy of desymmetrization of 1,3-cyclohexanedione by an intramolecular vinylation reaction of an enolate under palladium catalysis to give a strained bridgehead 1,3-cyclohexanedione scaffold. In the course of the study, a domino ring expansion was discovered and developed. Koumine (1) is a natural product isolated from the Gelsemium elegans, a… Expand

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+ ) m/z calcd for
    -nitrophenyl)oxonane-2,6-dione (22)
      3H) ppm; 13 C NMR (75 MHz, CDCl3): δ = 210
        ESI + ) m/z calcd for
          To a stirred solution of 21 (120 mg, 0.28 mmol, 1 equiv) in anhydrous THF (2.5 mL) was added PPh3