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Catalytic enantioselective nitrone cycloadditions enabling collective syntheses of indole alkaloids

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  • Xiaochen Tian

    (Ocean University of China
    Qingdao Marine Science and Technology Center)

  • Tengfei Xuan

    (Ocean University of China
    Qingdao Marine Science and Technology Center)

  • Jingkun Gao

    (Zhejiang University of Technology)

  • Xinyu Zhang

    (Ocean University of China)

  • Tao Liu

    (Ocean University of China)

  • Fengbiao Luo

    (Ocean University of China)

  • Ruochen Pang

    (Ocean University of China)

  • Pengcheng Shao

    (Ocean University of China)

  • Yun-Fang Yang

    (Zhejiang University of Technology)

  • Yang Wang

    (Ocean University of China
    Qingdao Marine Science and Technology Center)

Abstract

Tetrahydro-β-carboline skeletons are prominent and ubiquitous in an extraordinary range of indole alkaloid natural products and pharmaceutical compounds. Powerful synthetic approaches for stereoselective synthesis of tetrahydro-β-carboline skeletons have immense impacts and have attracted enormous attention. Here, we outline a general chiral phosphoric acid catalyzed asymmetric 1,3-dipolar cycloaddition of 3,4-dihydro-β-carboline-2-oxide type nitrone that enables access to three types of chiral tetrahydro-β-carbolines bearing continuous multi-chiral centers and quaternary chiral centers. The method displays different endo/exo selectivity from traditional nitrone chemistry. The distinct power of this strategy has been illustrated by application to collective and enantiodivergent total syntheses of 40 tetrahydro-β-carboline-type indole alkaloid natural products with divergent stereochemistry and varied architectures.

Suggested Citation

  • Xiaochen Tian & Tengfei Xuan & Jingkun Gao & Xinyu Zhang & Tao Liu & Fengbiao Luo & Ruochen Pang & Pengcheng Shao & Yun-Fang Yang & Yang Wang, 2024. "Catalytic enantioselective nitrone cycloadditions enabling collective syntheses of indole alkaloids," Nature Communications, Nature, vol. 15(1), pages 1-15, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-50509-4
    DOI: 10.1038/s41467-024-50509-4
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