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- W2959913426 abstract "Author(s): Holmbo, Stephen Daniel | Advisor(s): Pronin, Sergey V | Abstract: In Chapter One the isolation, biosynthesis, and bioactivity of the anthraquinone–xanthone heterodimers is discussed. Additionally, a review of previous synthetic effortstowards this class of natural products is provided, along with reported syntheses of relatedanthraquinone- and xanthone-derived natural products.Chapter Two discusses synthetic efforts towards the anthraquinone–xanthoneheterodimer natural products. This includes model system studies aimed at the constructionof the bicyclo[3.2.2]nonane core, as well as our first generation synthesis of thebenzocycloheptenone precursor. Our optimized route involves the development of aniodine(III)-mediated arylation enol ethers, which allows for rapid construction of a keyintermediate in the synthesis. A Hauser–Kraus annulation–aldol reaction sequence enablesassembly of the bicyclo[3.2.2]nonane core, which is then carried on to complete the first totalsynthesis of acremoxanthone A in 10 steps from commercial material.xvIn Chapter Three an overview of previously reported methods for the alkenylation ofketones is provided, followed by the development of the intermolecular In(III)-catalyzedalkenylation of silyl enol ethers with alkynes. This reaction is demonstrated on a variety ofcyclic and acyclic substrates to provide the corresponding 2-siloxy-1,4-dienes, via a formalene reaction, or β,γ-unsaturated ketones. Additionally, mechanistic investigations arediscussed, including a proposed mechanism for the intermolecular formal ene reaction." @default.
- W2959913426 created "2019-07-23" @default.
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- W2959913426 date "2019-01-01" @default.
- W2959913426 modified "2023-09-27" @default.
- W2959913426 title "Total Synthesis of Anthraquinone–Xanthone Natural Products and Intermolecular Alkenylation of Silyl Enol Ethers" @default.
- W2959913426 hasPublicationYear "2019" @default.
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