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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
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dc.contributor.advisor | 方俊民(Jim-Min Fang) | |
dc.contributor.author | Che-Sheng Hsu | en |
dc.contributor.author | 許哲生 | zh_TW |
dc.date.accessioned | 2021-06-15T16:37:46Z | - |
dc.date.available | 2025-08-01 | |
dc.date.copyright | 2015-08-28 | |
dc.date.issued | 2015 | |
dc.date.submitted | 2015-08-12 | |
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/52987 | - |
dc.description.abstract | 安卓奎諾爾(antroquinonol)屬於泛醌類(ubiquinone)的化合物,從牛樟芝的發酵菌絲體所分離得到,被發現具有抑制癌細胞及抗發炎作用。從牛樟芝取得安卓奎諾爾化合物產量很少,因此化學家們希望可藉由化學合成方式來直接獲得,同時驗證其立體化學及絕對組態。 安卓奎諾爾的結構骨架為2,3-二甲氧基環己-2-烯酮,並且由甲基、 菌綠烯醇基(farnesyl)及羥基建構三個立體中心。本論文第一階段以2,3,4-三甲氧基苯甲醛為起始物,經由拜耳–維立格氧化反應(Baeyer–Villiger oxidation)、苯酚氧化反應、麥克爾加成反應 (Michael addition)、烷基化反應、還原反應、水解反應及立體異構化簡短的7步驟,獲得(±)-安卓奎諾爾及其七個同類物。此麥克爾加成反應為第一個使用在具有四個甲氧基的多電子環己二烯酮的系統。 第二階段,發展針對多取代基環己二烯酮的系統進行不對稱催化麥克爾加成反應,可得到高效能鏡像選擇性的結果。接著將此方法,應用第一階段的天然物合成策略,可以獲得(+)-antroquinonol及(+)-antroquinonol D。 | zh_TW |
dc.description.abstract | Antroquinonol, isolated in low quantity from an endemic mushroom Antrodia cinnamomea, is under clinical evaluation in patients with non-small cell lung cancer. An efficient synthesis of antroquinonol is desired to meet the medicinal need. Antroquinonol has an unusual core structure of 2,3-dimethoxycyclohex-2-enone with methyl, farnesyl and hydroxyl substituents at three contiguous stereocenters. First, starting from 2,3,4-trimethoxybenzaldehyde, a concise synthesis of (±)-antroquinonol and its seven analogues was accomplished in 7 steps comprising Baeyer–Villiger oxidation, phenol oxidation, Michael reaction, alkylation, reduction, hydrolysis and epimerization. This study demonstrates the first example for Michael reaction in a highly electron-rich cyclohexadienone system carrying four electron-donating methoxy substituents. The asymmetry catalytic conjugate additions to substituted- 4,4-dimethoxycyclohexadienones were then achieved in high enantioselective manner, and applied to the syntheses of (+)-antroquinonol and (+)-antroquinonol D in a concise manner. | en |
dc.description.provenance | Made available in DSpace on 2021-06-15T16:37:46Z (GMT). No. of bitstreams: 1 ntu-104-D00223117-1.pdf: 28710629 bytes, checksum: d94055f71379ac5ac85adaa89ace24f9 (MD5) Previous issue date: 2015 | en |
dc.description.tableofcontents | 謝誌 I 中文摘要 II 英文摘要 III 目錄 IV 圖目錄 V 流程目錄 VII 表目錄 VIII 簡稱用語對照表 IX 緒論 1 牛樟芝的介紹 1 Antroquinonol 的來源及生物活性 1 Antroquinonol在老鼠體內的代謝物 5 Antroquinonol 及antroquinonol D的合成介紹 5 Cyclohexadienone的合成應用: 12 結果與討論 14 Antroquinonol及相似結構之合成 14 Antroquinonol的逆合成分析 20 2,3,4,4-四烷氧基環己二烯酮的不對稱共軛加成反應之探討 50 其他環己二烯酮的不對稱共軛加成反應之探討 53 結論 61 實驗部分 62 參考文獻 113 附錄:化合物之核磁共振光譜,HPLC及X-射線結晶圖 | |
dc.language.iso | zh-TW | |
dc.title | 安卓奎諾爾及其類似物之合成研究 | zh_TW |
dc.title | Synthesis of Antroquinonol and its Analogues | en |
dc.type | Thesis | |
dc.date.schoolyear | 103-2 | |
dc.description.degree | 博士 | |
dc.contributor.oralexamcommittee | 汪根欉(Ken-Tsung Wong),王宗興(Tsung-Shing Andrew Wang),吳世雄(Shih-Hsiung Wu),陳榮傑(Rong-Jie Chein),謝俊結(Jiun-Jie Shie) | |
dc.subject.keyword | 安卓奎諾爾,泛?類,麥克爾加成反應,多取代基環己二烯酮,不對稱催化麥克爾加成反應, | zh_TW |
dc.subject.keyword | antroquinonol,ubiquinone,substituted- 4,4-dimethoxycyclohexadienones,asymmetry catalytic conjugate additions, | en |
dc.relation.page | 305 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2015-08-12 | |
dc.contributor.author-college | 理學院 | zh_TW |
dc.contributor.author-dept | 化學研究所 | zh_TW |
顯示於系所單位: | 化學系 |
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