期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 50, 页码 13826-13829出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409038
关键词
alkaloids; asymmetric synthesis; cascade reactions; gephyrotoxin; total synthesis
资金
- European Research Council (ERC) [259056]
- Diamond Light Source [MT9981]
A concise and efficient synthesis of (-)-gephyrotoxin from L-pyroglutaminol has been realized. The key step in this approach is a diastereoselective intramolecular enamine/Michael cascade reaction that forms two rings and two stereocenters and generates a stable tricyclic iminium cation. A hydroxy-directed reduction of this intermediate plays a key role in establishing the required cis-decahydroquinoline ring system, enabling the total synthesis of (-)-gephyrotoxin in nine steps and 14% overall yield. The absolute configuration of the synthetic material was confirmed by single-crystal X-ray diffraction and is consistent with the structure originally proposed for material isolated from the natural source.
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