期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 40, 页码 14216-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja906429c
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资金
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- University of Alberta
- Alberta Ingenuity Foundation
- DAAD (Germany)
A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.
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