State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China).
Angew Chem Int Ed Engl. 2014 Aug 18;53(34):9012-6. doi: 10.1002/anie.201404191. Epub 2014 Jun 24.
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.
首次完成了 sespenine 的全合成，这是一种来自红树林内生真菌的罕见吲哚倍半萜。受生物启发的氮杂-Prins/Friedel-Crafts/逆 Friedel-Crafts 级联反应构建了桥环四氢喹啉核心。对氮杂-Prins 环化反应的进一步研究表明，羟吲哚啉中间体的 C3 构型对于 sespenine 及其同系物 xiamycin A 的生物合成至关重要。
