期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 39, 页码 11824-11828出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201605475
关键词
C-H activation; desymmetrization; indole alkaloids; indolization; natural products
资金
- US National Science Foundation (NSF) CCI Center for Selective C-H Functionalization [CHE-1205646]
- US NSF Graduate Research Fellowship [DGE-1106400]
- Leopoldina Postdoctoral Fellowship [LPDS 2013-05]
- NSF-CCI Center for Selective C-H Functionalization
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1205646] Funding Source: National Science Foundation
We describe herein formal syntheses of the indole alkaloids cis-trikentrin A and herbindole B from a common meso-hydroquinone intermediate prepared by a ruthenium-catalyzed [2+2+1+1] cycloaddition that has not been used previously in natural product synthesis. Key steps include a sterically demanding Buchwald-Hartwig amination as well as a unique C(sp(3))-H amination/indole formation. Studies toward a selective desymmetrization of the meso-hydroquinone are also reported.
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