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Bioinspired Total Synthesis of Sespenine

Authors

  • Yu Sun,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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    • These authors contributed equally to this work.

  • Pengxi Chen,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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    • These authors contributed equally to this work.

  • Deliang Zhang,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • Martin Baunach,

    1. Leibniz Institute for Natural Product Research and Infection Biology, HKI, Jena (Germany)
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  • Prof. Dr. Christian Hertweck,

    1. Leibniz Institute for Natural Product Research and Infection Biology, HKI, Jena (Germany)
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  • Prof. Dr. Ang Li

    Corresponding author
    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
    • State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)

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  • We thank Qingbo Zhang and Prof. Changsheng Zhang for helpful discussions. Financial support was provided by the Ministry of Science & Technology (2013CB836900) and National Natural Science Foundation of China (21290180, 21172235, and 21222202).

Abstract

The first total synthesis of sespenine, a rare indole sesquiterpenoid from a mangrove endophyte, has been accomplished. A bioinspired aza-Prins/Friedel–Crafts/retro Friedel–Crafts cascade reaction assembles the bridged tetrahydroquinoline core. Further investigations on the aza-Prins cyclization imply that the C3 configuration of the hydroxyindolenine intermediate is crucial to the biosynthesis of sespenine and its congener xiamycin A.

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