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Titanium catalyzed [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes with 1,3-dienes for efficient synthesis of stilbene bioisosteres

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  • Yonghong Liu

    (Cancer Hospital of Dalian University of Technology
    Dalian University of Technology)

  • Zhixian Wu

    (Cancer Hospital of Dalian University of Technology
    Dalian University of Technology)

  • Jing-Ran Shan

    (University of California Los Angeles)

  • Huaipu Yan

    (Dalian University of Technology)

  • Er-Jun Hao

    (Henan Normal University)

  • Lei Shi

    (Cancer Hospital of Dalian University of Technology
    Dalian University of Technology
    Henan Normal University)

Abstract

Natural stilbenes have shown significant potential in the prevention and treatment of diseases due to their diverse pharmacological activities. Here we present a mild and effective Ti-catalyzed intermolecular radical-relay [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes and 1,3-dienes. This transformation enables the synthesis of bicyclo[2.1.1]hexane (BCH) scaffolds containing aryl vinyl groups with excellent regio- and trans-selectivity and broad functional group tolerance, thus offering rapid access to structurally diverse stilbene bioisosteres.

Suggested Citation

  • Yonghong Liu & Zhixian Wu & Jing-Ran Shan & Huaipu Yan & Er-Jun Hao & Lei Shi, 2024. "Titanium catalyzed [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes with 1,3-dienes for efficient synthesis of stilbene bioisosteres," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-48494-9
    DOI: 10.1038/s41467-024-48494-9
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    3. Marie L. J. Wong & Alistair J. Sterling & James J. Mousseau & Fernanda Duarte & Edward A. Anderson, 2021. "Direct catalytic asymmetric synthesis of α-chiral bicyclo[1.1.1]pentanes," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
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    5. Mario P. Wiesenfeldt & James A. Rossi-Ashton & Ian B. Perry & Johannes Diesel & Olivia L. Garry & Florian Bartels & Susannah C. Coote & Xiaoshen Ma & Charles S. Yeung & David J. Bennett & David W. C. , 2023. "General access to cubanes as benzene bioisosteres," Nature, Nature, vol. 618(7965), pages 513-518, June.
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