Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 34, Pages 9012-9016Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404191
Keywords
biomimetic synthesis; cyclization; heterocycles; natural products; total synthesis
Categories
Funding
- Ministry of Science Technology [2013CB836900]
- National Natural Science Foundation of China [21290180, 21172235, 21222202]
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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.
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