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| 研究生： |
吳欣穎 Hsin-Ying Wu |
|---|---|
| 論文名稱： |
Nabscessin A的不對稱合成 |
| 指導教授： |
侯敦仁
Duen-Ren Hou |
| 口試委員: | |
| 學位類別： |
碩士 Master |
| 系所名稱： |
理學院 - 化學學系 Department of Chemistry |
| 論文出版年： | 2020 |
| 畢業學年度： | 108 |
| 語文別： | 中文 |
| 論文頁數： | 202 |
| 中文關鍵詞： | 不對稱合成 |
| 外文關鍵詞： | Nabscessin A |
| 相關次數： | 點閱：5 下載：0 |
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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 .
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