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

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Title
Rearrangements of the Chrysanthenol Core: Application to a Formal Synthesis of Xishacorene B
Author(s)
Jones, Kerry E.; Bohyun Park; Doering, Nicolle A.; Mu-Hyun Baik; Sarpong, Richmond
Publication Date
2021-12
Journal
Journal of the American Chemical Society, v.143, no.48, pp.20482 - 20490
Publisher
American Chemical Society
Abstract
© 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 Suárez 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.
URI
https://pr.ibs.re.kr/handle/8788114/10849
DOI
10.1021/jacs.1c10804
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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