期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 20, 页码 6112-6119出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201400178
关键词
cascade reactions; conjugate additions; divergent total synthesis; enantioselective catalysis; octahydroindolones
资金
- NSFC [21162034, 21372193, 21362040]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT13095]
- Ministry of Education of China [20135301110002]
- Government of Yunnan Province [2012FB114, 2013 A026]
We report the first catalytic asymmetric approach to octahydroindolones and a divergent enantioselective synthesis of perhydroindole alkaloids, as exemplified by lycorine-type Amaryllidaceae alkaloids (+)--lycorane and (+)-lycorine, from a common intermediate by using a highly concise route. The assembly of octahydroindolones employs a catalytic enantioselective 1,4-conjugate addition of nitro dienynes, followed by a TsOH-catalyzed cascade synthesis of highly functionalized enones, and a diastereoselective intramolecular Michael addition.
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