Bioinspired total synthesis of sespenine.

Sun Y, Chen P, Zhang D, Baunach M, Hertweck C, Li A (2014) Bioinspired total synthesis of sespenine. Angew Chem Int Ed Engl 53(34), 9012-9016. PubMed


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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doi: 10.1002/anie.201404191 PMID: 24962149