Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 1, Pages 350-353Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609975
Keywords
natural products; oxidation; rearrangements; ring contraction; total synthesis
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Funding
- National Natural Science Foundation of China [21672171, 21372239, 21202187]
- Scientific Research Foundation of Northwest AF University [Z111021501, Z109021600]
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Oxidative ring contraction of cyclic a-formyl ketones was facilitated by the action of H2O2 under operationally simple and environmentally benign reaction conditions. The process was highly regioselective and enables stereospecific construction of contiguous quaternary all-carbon centers from stereodefined all-substituted all-cyclic ketones. The asymmetric syntheses of (+)-cuparene and (+)-tochuinyl acetate were also successively achieved by taking advantage of this novel protocol.
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