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.


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.


Christian Hertweck
Martin Baunach


doi: 10.1002/anie.201404191

PMID: 24962149