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

Kemiao Hong, Mengting Liu, Lixin Qian, Ming Bao, Gang Chen, Xinyu Jiang, Jingjing Huang and Xinfang Xu ()
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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

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-49664-5

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