期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 36, 页码 10830-10834出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706273
关键词
alkaloids; cascade reactions; directed lithiation; total synthesis; virosaine A
资金
- Natural Science and Engineering Research Council of Canada (NSERC)
- NSERC
- Walter C. Sumner Foundation
The total synthesis of (-)-virosaine A (1) was achieved in ten steps starting from furan and 2-bromoacrolein. A one-pot Diels-Alder cycloaddition/organolithium addition initiated an efficient sequence to access a key oxime/epoxide intermediate. Heating this intermediate in acetic acid resulted in an intramolecular epoxide opening/nitrone [3+2] cycloaddition cascade to construct the caged core of 1 in a single step. Several methods of C-H functionalization were assessed on the cascade product, and ultimately, a directed lithiation/bromination effected selective C14 functionalization, enabling the synthesis of 1.
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