ArticleJournal of the American Chemical Society2021
Rearrangements of the Chrysanthenol Core: Application to a Formal Synthesis of Xishacorene B.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of α-Pinene.The Journal of organic chemistry · 2024Article
- Strategic application of C-H oxidation in natural product total synthesis.Nature reviews. Chemistry · 2023Review
- Skeletal diversification by C-C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate.Chemical communications (Cambridge, England) · 2023Article
- Chemistry and bioactivity of secondary metabolites from South China Sea marine fauna and flora: recent research advances and perspective.Acta pharmacologica Sinica · 2022Review
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Authors and funding
5 authors.
Funding
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.
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