Bioinspired Total Synthesis of Sespenine |
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| Authors: | Yu Sun Pengxi Chen Deliang Zhang Martin Baunach Prof. Dr. Christian Hertweck Prof. Dr. Ang Li |
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| Affiliation: | 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);2. Leibniz Institute for Natural Product Research and Infection Biology, HKI, Jena (Germany) |
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| 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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| Keywords: | biomimetic synthesis cyclization heterocycles natural products total synthesis |
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