Rearrangements of the Chrysanthenol Core: Application to a Formal Synthesis of Xishacorene B

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Reported here are substrate-dictated rearrangements of chrysanthenol derivatives prepared from verbenone to access complex bicyclic frameworks. These rearrangements set the stage for a 10-step formal synthesis of the natural product xishacorene B. Key steps include an anionic allenol oxy-Cope rearrangement and a Sua ' rez directed C-H functionalization. The success of this work was guided by extensive computational calculations which provided invaluable insight into the reactivity of the chrysanthenol-derived systems, especially in the key oxy-Cope rearrangement.
Publisher
AMER CHEMICAL SOC
Issue Date
2021-12
Language
English
Article Type
Article
Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.143, no.48, pp.20482 - 20490

ISSN
0002-7863
DOI
10.1021/jacs.1c10804
URI
http://hdl.handle.net/10203/292355
Appears in Collection
CH-Journal Papers(저널논문)
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