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Tandem C–H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (−)-brussonol and (−)-przewalskine E

Author

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  • Zhi-Wei Jiao

    (State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University)

  • Yong-Qiang Tu

    (State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University
    Collaborative Innovation Center of Chemical Science and Engineering)

  • Qing Zhang

    (State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University)

  • Wen-Xing Liu

    (State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University)

  • Shu-Yu Zhang

    (State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University)

  • Shao-Hua Wang

    (State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University)

  • Fu-Min Zhang

    (State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University)

  • Sen Jiang

    (State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University)

Abstract

Natural products are a vital source of lead compounds in drug discovery. Development of efficient tandem reactions to build useful compounds and apply them to the synthesis of natural products is not only a significant challenge but also an important goal for chemists. Here we describe a tandem C–H oxidation/cyclization/rearrangement of isochroman-derived allylic silylethers, promoted by DDQ and InCl3. This method allows the efficient construction of tricyclic benzoxa[3.2.1]octanes with a wide substrate scope. We employ this tandem reaction to achieve the asymmetric total syntheses of (−)-brussonol and (−)-przewalskine E.

Suggested Citation

  • Zhi-Wei Jiao & Yong-Qiang Tu & Qing Zhang & Wen-Xing Liu & Shu-Yu Zhang & Shao-Hua Wang & Fu-Min Zhang & Sen Jiang, 2015. "Tandem C–H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (−)-brussonol and (−)-przewalskine E," Nature Communications, Nature, vol. 6(1), pages 1-7, November.
    • Handle: RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms8332
    DOI: 10.1038/ncomms8332
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