Synthesis and structural revision of a brominated sesquiterpenoid, aldingenin C.

  title={Synthesis and structural revision of a brominated sesquiterpenoid, aldingenin C.},
  author={Shunya Takahashi and M. Yasuda and T. Nakamura and K. Hatano and K. Matsuoka and H. Koshino},
  journal={The Journal of organic chemistry},
  volume={79 19},
  • Shunya Takahashi, M. Yasuda, +3 authors H. Koshino
  • Published 2014
  • Medicine, Chemistry
  • The Journal of organic chemistry
  • This paper describes a short step synthesis of the proposed structure for aldingenin C from trans-limonene oxide. The tetrahydropyran-fused 2-oxabicyclo[3.2.2]nonane skeleton as the structural feature was constructed by an intramolecular epoxide-opening reaction and a brominative cyclization. The spectral data of the synthetic compound did not match those of the natural product reported. Re-examination of the reported NMR data using new CAST/CNMR Structure Elucidator suggests that the structure… CONTINUE READING
    7 Citations

    Figures, Tables, and Topics from this paper.

    Explore Further: Topics Discussed in This Paper

    Total Synthesis of the Proposed Structure for Aromin and Its Structural Revision.
    • 2
    • PDF
    Recent trends in the structural revision of natural products.
    • 25
    The Laurencia Paradox: An Endless Source of Chemodiversity.
    • 30


    Total synthesis of the proposed structure of aldingenin B.
    • 16
    Cytotoxic halogenated metabolites from the Brazilian red alga Laurencia catarinensis.
    • 52