title: Bioinspired total synthesis of sespenine.
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.
authors: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China).
authors: Yu
authors: Y
authors: Sun
authors: Pengxi
authors: P
authors: Chen
authors: Deliang
authors: D
authors: Zhang
authors: Martin
authors: M
authors: Baunach
authors: Christian
authors: C
authors: Hertweck
authors: Ang
authors: A
authors: Li
mesh_terms: D012717:Sesquiterpenes / Q000138:chemical synthesis*
chemical_list: D012717:Sesquiterpenes
keywords: biomimetic synthesis; cyclization; heterocycles; natural products; total synthesis