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Total Synthesis of Anthraquinone-Xanthone Natural Products and Intermolecular Alkenylation of Silyl Enol Ethers
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| 자료유형 | 학위논문 |
|---|---|
| 서명/저자사항 | Total Synthesis of Anthraquinone-Xanthone Natural Products and Intermolecular Alkenylation of Silyl Enol Ethers. |
| 개인저자 | Holmbo, Stephen Daniel. |
| 단체저자명 | University of California, Irvine. Chemistry - Ph.D.. |
| 발행사항 | [S.l.]: University of California, Irvine., 2019. |
| 발행사항 | Ann Arbor: ProQuest Dissertations & Theses, 2019. |
| 형태사항 | 368 p. |
| 기본자료 저록 | Dissertations Abstracts International 81-04B. Dissertation Abstract International |
| ISBN | 9781085655804 |
| 학위논문주기 | Thesis (Ph.D.)--University of California, Irvine, 2019. |
| 일반주기 |
Source: Dissertations Abstracts International, Volume: 81-04, Section: B.
Advisor: Pronin, Sergey V. |
| 이용제한사항 | This item must not be sold to any third party vendors. |
| 요약 | In Chapter One the isolation, biosynthesis, and bioactivity of the anthraquinone- xanthone heterodimers is discussed. Additionally, a review of previous synthetic efforts towards this class of natural products is provided, along with reported syntheses of related anthraquinone- and xanthone-derived natural products.Chapter Two discusses synthetic efforts towards the anthraquinone-xanthone heterodimer natural products. This includes model system studies aimed at the construction of the bicyclo[3.2.2]nonane core, as well as our first generation synthesis of the benzocycloheptenone precursor. Our optimized route involves the development of an iodine(III)-mediated arylation enol ethers, which allows for rapid construction of a key intermediate in the synthesis. A Hauser-Kraus annulation-aldol reaction sequence enables assembly of the bicyclo[3.2.2]nonane core, which is then carried on to complete the first total synthesis of acremoxanthone A in 10 steps from commercial material.In Chapter Three an overview of previously reported methods for the alkenylation of ketones is provided, followed by the development of the intermolecular In(III)-catalyzed alkenylation of silyl enol ethers with alkynes. This reaction is demonstrated on a variety of cyclic and acyclic substrates to provide the corresponding 2-siloxy-1,4-dienes, via a formal ene reaction, or 棺,款-unsaturated ketones. Additionally, mechanistic investigations are discussed, including a proposed mechanism for the intermolecular formal ene reaction. |
| 일반주제명 | Organic chemistry. Chemistry. |
| 언어 | 영어 |
| 바로가기 | 
: 이 자료의 원문은 한국교육학술정보원에서 제공합니다. |
