Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 19, Pages 6420-6424Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201902155
Keywords
bicyclo[3; 3; 1]nonanes; C-H functionalization; cross-coupling; cyclopropanol; total synthesis
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Funding
- NSFC [21672029, 21871033]
- CSTC [2018jcyjAX0421]
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Based on the discovery of copper-catalyzed cyclopropanol ring-opening addition to iminium ions, an unprecedented catalytic aerobic C-H oxidation/cyclopropanol cyclization cascade using CuCl2 as the multifunctional catalyst and air as the oxidant was developed to construct the azabicyclo[3.3.1]nonane skeleton, which is widespread in natural products and medicines. Using this method, concise asymmetric total synthesis of the indole alkaloid (-)-suaveoline was achieved. This study not only provides an efficient, low-cost, and environmentally benign method for constructing such bridged frameworks, but also enriches the realm of cyclopropanol chemistry and C-H functionalization.
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