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Catalytic [4+2]- and [4+4]-cycloaddition using furan-fused cyclobutanone as a privileged C4 synthon

Author

Listed:
  • Kemiao Hong

    (Zhejiang Sci-Tech University)

  • Mengting Liu

    (Sun Yat-sen University)

  • Lixin Qian

    (Sun Yat-sen University)

  • Ming Bao

    (Zhejiang Sci-Tech University)

  • Gang Chen

    (Sun Yat-sen University)

  • Xinyu Jiang

    (Sun Yat-sen University)

  • Jingjing Huang

    (Sun Yat-sen University)

  • Xinfang Xu

    (Zhejiang Sci-Tech University)

Abstract

Cycloaddition reactions play a pivotal role in synthetic chemistry for the direct assembly of cyclic architectures. However, hurdles remain for extending the C4 synthon to construct diverse heterocycles via programmable [4+n]-cycloaddition. Here we report an atom-economic and modular intermolecular cycloaddition using furan-fused cyclobutanones (FCBs) as a versatile C4 synthon. In contrast to the well-documented cycloaddition of benzocyclobutenones, this is a complementary version using FCB as a C4 reagent. It involves a C-C bond activation and cycloaddition sequence, including a Rh-catalyzed enantioselective [4 + 2]-cycloaddition with imines and an Au-catalyzed diastereoselective [4 + 4]-cycloaddition with anthranils. The obtained furan-fused lactams, which are pivotal motifs that present in many natural products, bioactive molecules, and materials, are inaccessible or difficult to prepare by other methods. Preliminary antitumor activity study indicates that 6e and 6 f exhibit high anticancer potency against colon cancer cells (HCT-116, IC50 = 0.50 ± 0.05 μM) and esophageal squamous cell carcinoma cells (KYSE-520, IC50 = 0.89 ± 0.13 μM), respectively.

Suggested Citation

  • Kemiao Hong & Mengting Liu & Lixin Qian & Ming Bao & Gang Chen & Xinyu Jiang & Jingjing Huang & Xinfang Xu, 2024. "Catalytic [4+2]- and [4+4]-cycloaddition using furan-fused cyclobutanone as a privileged C4 synthon," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-49664-5
    DOI: 10.1038/s41467-024-49664-5
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    References listed on IDEAS

    as
    1. Jianyu Zhang & Xi Wang & Tao Xu, 2021. "Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+4] cycloaddition," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
    2. Kemiao Hong & Yi Zhou & Haoxuan Yuan & Zhijing Zhang & Jingjing Huang & Shanliang Dong & Wenhao Hu & Zhi-Xiang Yu & Xinfang Xu, 2023. "Catalytic 4-exo-dig carbocyclization for the construction of furan-fused cyclobutanones and synthetic applications," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    3. Changgui Zhao & Zhengqing Ye & Zhi-xiong Ma & Scott A. Wildman & Stephanie A. Blaszczyk & Lihong Hu & Ilia A. Guizei & Weiping Tang, 2019. "A general strategy for diversifying complex natural products to polycyclic scaffolds with medium-sized rings," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
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