These authors contributed equally to this work.
Bioinspired Total Synthesis of Sespenine†
Article first published online: 24 JUN 2014
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 53, Issue 34, pages 9012–9016, August 18, 2014
How to Cite
Sun, Y., Chen, P., Zhang, D., Baunach, M., Hertweck, C. and Li, A. (2014), Bioinspired Total Synthesis of Sespenine. Angew. Chem. Int. Ed., 53: 9012–9016. doi: 10.1002/anie.201404191
We thank Qingbo Zhang and Prof. Changsheng Zhang for helpful discussions. Financial support was provided by the Ministry of Science & Technology (2013CB836900) and National Natural Science Foundation of China (21290180, 21172235, and 21222202).
- Issue published online: 13 AUG 2014
- Article first published online: 24 JUN 2014
- Manuscript Received: 10 APR 2014
- Ministry of Science & Technology. Grant Number: 2013CB836900
- National Natural Science Foundation of China. Grant Numbers: 21290180, 21172235, 21222202
- biomimetic synthesis;
- natural products;
- total synthesis
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.