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    Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/83287


    Title: Nabscessin A的不對稱合成
    Authors: 吳欣穎;Wu, Hsin-Ying
    Contributors: 化學學系
    Keywords: 不對稱合成;Nabscessin A
    Date: 2020-08-20
    Issue Date: 2020-09-02 15:18:55 (UTC+8)
    Publisher: 國立中央大學
    Abstract: ent-Nabscessin A (2)是由市售的肌醇(myo-inositol)與右旋樟腦二縮醛(dimethyl D-camphor acetal)經由14步合成出來。天然物Nabscessin A (1)的形式合成則是由化合物(-)-70經由化合物(+)-70後續合成ent-Nabscessin A (2)之步驟完成。
    此合成的特點是利用肌醇(myo-inositol)原有的六元環架構經由選擇性去氧(deoxygenation)、以疊氮化鈉(sodium azide, NaN3)作為親核試劑進行SN2反應生成碳氮鍵、施陶丁格反應(Staudinger reduction)等步驟,得到其關鍵中心脫氧胺基鯊肌醇(2-deoxy-scyllo-inosamine, DOIA)此種結構。中心核心再經由選擇性酯化等一系列反應生成目標產物。
    ;Enantiomer of Nabscessin A (2) was synthesized from commercial available myo-inositol and dimethyl D-camphor acetal in 14 steps. Formal synthesis of natural Nabscessin A (1) was also achieved by the compound (-)-70, and followed by the steps of compound (+)-70 synthesized enantiomer of Nabscessin A (2).
    This synthesis features utilizations of the existing framework of myo-inositol and subsequent transformations, including selective deoxygenation, amino group formation, Staudinger reaction etc, provided the key 2-deoxy-scyllo-inosamine core. The DOIA core then completes the synthesis of our target product through a series of reactions such as selective esterification .
    Appears in Collections:[化學研究所] 博碩士論文

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