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Bioinspired Total Synthesis of Sespenine
Author(s) -
Sun Yu,
Chen Pengxi,
Zhang Deliang,
Baunach Martin,
Hertweck Christian,
Li Ang
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404191
Subject(s) - total synthesis , prins reaction , friedel–crafts reaction , chemistry , indole test , stereochemistry , biomimetic synthesis , cascade , biosynthesis , organic chemistry , catalysis , enzyme , chromatography
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.