| LDR | | 00000nam u2200205 4500 |
| 001 | | 000000432508 |
| 005 | | 20200224131707 |
| 008 | | 200131s2019 ||||||||||||||||| ||eng d |
| 020 | |
▼a 9781085655804 |
| 035 | |
▼a (MiAaPQ)AAI13897713 |
| 040 | |
▼a MiAaPQ
▼c MiAaPQ
▼d 247004 |
| 082 | 0 |
▼a 540 |
| 100 | 1 |
▼a Holmbo, Stephen Daniel. |
| 245 | 10 |
▼a Total Synthesis of Anthraquinone-Xanthone Natural Products and Intermolecular Alkenylation of Silyl Enol Ethers. |
| 260 | |
▼a [S.l.]:
▼b University of California, Irvine.,
▼c 2019. |
| 260 | 1 |
▼a Ann Arbor:
▼b ProQuest Dissertations & Theses,
▼c 2019. |
| 300 | |
▼a 368 p. |
| 500 | |
▼a Source: Dissertations Abstracts International, Volume: 81-04, Section: B. |
| 500 | |
▼a Advisor: Pronin, Sergey V. |
| 502 | 1 |
▼a Thesis (Ph.D.)--University of California, Irvine, 2019. |
| 506 | |
▼a This item must not be sold to any third party vendors. |
| 520 | |
▼a 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. |
| 590 | |
▼a School code: 0030. |
| 650 | 4 |
▼a Organic chemistry. |
| 650 | 4 |
▼a Chemistry. |
| 690 | |
▼a 0490 |
| 690 | |
▼a 0485 |
| 710 | 20 |
▼a University of California, Irvine.
▼b Chemistry - Ph.D.. |
| 773 | 0 |
▼t Dissertations Abstracts International
▼g 81-04B. |
| 773 | |
▼t Dissertation Abstract International |
| 790 | |
▼a 0030 |
| 791 | |
▼a Ph.D. |
| 792 | |
▼a 2019 |
| 793 | |
▼a English |
| 856 | 40 |
▼u http://www.riss.kr/pdu/ddodLink.do?id=T15491861
▼n KERIS
▼z 이 자료의 원문은 한국교육학술정보원에서 제공합니다. |
| 980 | |
▼a 202002
▼f 2020 |
| 990 | |
▼a ***1008102 |
| 991 | |
▼a E-BOOK |