Bioinspired Total Synthesis of Sespenine1. Issue 34 (24th June 2014)

• Record Type: Journal Article
• Authors: Sun, Yu; Chen, Pengxi; Zhang, Deliang; Baunach, Martin; Hertweck, Christian; Li, Ang
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 34(2014)
• Page Start: 9012
• Page End: 9016
• Publication Date: 2014-06-24
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201404191
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>