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Syntheses of piperidine alkaloid (–)-pelletierine, (–)-homopipecolic acid and indole alkaloid physostigmine
Authors
Chien-Lun Kao
高健倫
Publication date
6 June 2014
Publisher
化學系所
Abstract
本篇論文主要為對含氮雜環生物鹼之合成路徑開發與反應條件探討。共分為二個部分,第一部分為吲哚植物鹼physostigmine之合成研究:將本實驗室一直以來致力研究的骨牌式氫甲醯化反應/雙環化反應,應用於雙胺基烯類衍生物70,進行骨牌式二次環合反應,建立三環hexahydropyrrolo[2,3-b]indoline的骨架71,並可應用於富有生物活性之植物鹼physostigmine及其衍生物的合成研究。 第二部分為哌啶植物鹼 (–)-pelletierine與 (–)-homopipecolic acid的合成研究:延續本實驗室已開發之胺基醇118和酮類120之製備,以Bayer-Villiger氧化反應得到內酯121,並還原得到哌啶結構衍生物122,並進一步合成植物鹼 (–)-homopipecolic acid及 (–)-pelletierine。Piperidine and indole alkaloids are medicinal compounds with potent biological activity activities. Here described syntheses of (–)-piperidine alkaloids (–)-pelletierine and (–)-homopipecolic acid, featuring a Bayer-Villiger oxidation of 6-tropanone as the key step; and synthetic studies on physostigmine and esermethole as applications of the Rh-catalyzed hydroformylation / double cyclization reaction.第一章 毒扁豆鹼之合成研究 1 1.1 毒扁豆鹼之簡介 1 1.2 利用氫甲醯化反應進行骨牌式反應 10 1.2.1 縮醛 10 1.2.2 縮醛胺 13 1.2.3 亞胺 13 1.2.4 烯胺 14 1.3 研就動機 16 1.4 結果與討論 18 1.4.1 逆合成分析 (一) 18 1.4.2 合成探討(一) 19 1.4.3 逆合成分析 (二) 27 1.4.4 合成探討(二) 28 1.5 結論 33 第二章 手性2,6-二取代哌啶衍生物之合成研究 34 2.1 2,6-二取代哌啶衍生物之介紹 34 2.2 結果與討論 37 2.3 結論 45 實驗部份 46 儀器測定與試劑 46 實驗部步驟 48 參考文獻 79 附錄一 Syntheses of (−)-pelletierine and (−)-homopipecolic acid 13
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Last time updated on 16/06/2016