Convenient Synthesis of Angular Triquinane from 4-Alkenylfulvene via Thermal Cycloaddition Followed by Skeletal Rearrangement of the Resulting [4 + 2] Adduct

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  • Sho Inagaki
    Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui
  • Keisuke Imura
    Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui
  • Toshio Morita
    Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui
  • Yasuharu Yoshimi
    Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui
  • Minoru Hatanaka
    Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui
  • Tomikazu Kawano
    School of Pharmacy, Iwate Medical University

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Abstract

<jats:title>Abstract</jats:title> <jats:p>Alkenylfulvene prepared by the annulation of allylidenetriphenylphosphorane with 1,4-ynedione proceeded thermal cycloaddition in a highly regio- and stereoselective manner to give [4 + 2] adduct which was then converted into triquinane derivative by the treatment with LHMDS-t-BuOK after hydrolysis of the enol ether group.</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 37 (4), 454-455, 2008-03-15

    Oxford University Press (OUP)

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