| DC 欄位 |
值 |
語言 |
| DC.contributor | 化學學系 | zh_TW |
| DC.creator | 趙翊豪 | zh_TW |
| DC.creator | I-hao Chao | en_US |
| dc.date.accessioned | 2015-1-30T07:39:07Z | |
| dc.date.available | 2015-1-30T07:39:07Z | |
| dc.date.issued | 2015 | |
| dc.identifier.uri | http://ir.lib.ncu.edu.tw:444/thesis/view_etd.asp?URN=101223044 | |
| dc.contributor.department | 化學學系 | zh_TW |
| DC.description | 國立中央大學 | zh_TW |
| DC.description | National Central University | en_US |
| dc.description.abstract | 從凹唇薑(或稱高良薑)身上萃取出的(–)-panduratin D被檢驗在營養喪失的條件下，有些許抗人類胰腺癌細胞活性，然而至今沒有關於(–)-panduratin D的全合成文獻發表。我們以3-甲氧苯酚作為起始物，經由10步合成成功得到外消旋panduratin D。關鍵步驟包含使用鄰位陰離子夫裏士重排(anionic ortho-Fries rearrangement)及薗頭耦合合環(Sonogashira coupling annulation)反應來建構苯并呋喃的本體結構、鄰位定向硼酸鹽氧化反應、醯胺的烷化反應、醛醇縮合作用，以及最後在狄耳士-阿德爾反應後建立此化合物的立體中心。確定路徑後，我們在最後一步嘗試做狄耳士-阿德爾的不對稱反應來得到單一的鏡像異構物；我們也嘗試做羥基定向烷化反應取代親核性烷基鋰試劑的使用。 | zh_TW |
| dc.description.abstract | (–)-panduratin D, isolated from Boesenbergia pandurate, was examined a mild activity against human pancreatic PANC-1 cancer cells under nutrient-deprived conditions. We first synthesized racemic panduratin D from 3-methoxyphenol in 10 steps. The key features included construction of benzofuran system by anionic ortho-Fries rearrangement and Sonogashira coupling annulation of 2-iodo-3-methoxyphenyl diethylcarbamate, directed ortho borate oxidation, alkylation of amide, aldol condensation, as well as Diels-Alder reaction, which established the stereocenter. Later, we tried some enantioselective Diels-Alder reactions expected to afford single enantiomer; we also tried applying hydroxyl-directed alkylation in place of alkylation with nucleophilic alkyl lithium reagent. | en_US |
| DC.subject | 狄耳士-阿德爾反應 | zh_TW |
| DC.subject | 羥基定向烷化反應 | zh_TW |
| DC.subject | panduratin D | en_US |
| DC.subject | Diels-Alder reaction | en_US |
| DC.subject | hydroxyl-directed alkylation | en_US |
| DC.title | Total Synthesis of (±)-Panduratin D | en_US |
| dc.language.iso | en_US | en_US |
| DC.type | 博碩士論文 | zh_TW |
| DC.type | thesis | en_US |
| DC.publisher | National Central University | en_US |