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

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.

SUBMITTER: Jones KE

PROVIDER: S-EPMC9177077 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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

Jones Kerry E KE Park Bohyun B Doering Nicolle A NA Baik Mu-Hyun MH Sarpong Richmond R

Journal of the American Chemical Society 20211123 48

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 chrysanthe ...[more]

PMID: 34812038

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