Bioinspired Total Synthesis of Sespenine

被引：77
作者：
Sun, Yu [1 ]
Chen, Pengxi [1 ]
Zhang, Deliang [1 ]
Baunach, Martin [2 ]
Hertweck, Christian [2 ]
Li, Ang [1 ]
机构：
[1] Chinese Acad Sci, State Key Lab Bioorgan & Nat Prod Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
[2] HKI, Leibniz Inst Nat Prod Res & Infect Biol, Jena, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 34期
基金：
中国国家自然科学基金;
关键词：
biomimetic synthesis; cyclization; heterocycles; natural products; total synthesis; RING-SYSTEM; OXIDATIVE REARRANGEMENT; ASPERGILLUS-NOMIUS; INDOLE; CYCLIZATION; ALKALOIDS; TETRAHYDROQUINOLINES; BIOSYNTHESIS; DERIVATIVES; ASPERNOMINE;
D O I：
10.1002/anie.201404191
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：9012 / 9016
页数：5
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