| DC 欄位 |
值 |
語言 |
| DC.contributor | 化學學系 | zh_TW |
| DC.creator | 江孟軒 | zh_TW |
| DC.creator | MENG-HSUAN CHIANG | en_US |
| dc.date.accessioned | 2011-10-27T07:39:07Z | |
| dc.date.available | 2011-10-27T07:39:07Z | |
| dc.date.issued | 2011 | |
| dc.identifier.uri | http://ir.lib.ncu.edu.tw:88/thesis/view_etd.asp?URN=982203051 | |
| 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 | 在 1991 年，Nozoe 教授發現巴西大橶科植物Favela 表皮的甲醇
萃取液對P-388 淋巴血癌細胞具有細胞毒性，進而分離出Faveline
methyl ether，至今已有四篇全合成的文獻發表。我們希望縮短合成路
徑，採用5-exo-dig 合環-Claisen 重排聯繼反應於合成Faveline methyl
ether 最後一步的合環反應。首先我們從化合物9 及33 開始，分別以
四個和七個合成步驟得到化合物3 及23，接著將這兩部分結合，去
保護後得到中間體1 做為5-exo-dig 合環-Claisen 重排聯繼反應的前
驅物。在一系列的反應條件下只得到產物44，我們轉而將此聯繼反
應拆開，希望以不同的催化反應先得到5-exo-dig 合環的中間體42，
再進行Claisen 重排反應得到Faveline methyl ether。而另一方面也對
不對稱合成做相關探討。
| zh_TW |
| dc.description.abstract | In 1991, Professor Nozoe et al. isolated faveline methyl ether from
the methanolic extracts of the bark of Favela which showed the
bioactivity against P-388 lymphocytic leukemia in cell culture. There are
four total syntheses of faveline methyl ether reported. In this thesis, we
planned to shorten the synthetic steps by applying 5-exe-dig cyclization
/Claisen rearrangement as a cyclization key step. First, 3 and 23 were
synthesized in four and seven steps respectively from 9 and 33, followed
by nucleophilic attack and terminal alkyne deprotection to generate
intermediate 1 as a precursor of 5-exo-dig cyclization/Claisen rearrangement.
Unfortunately, only compound 44 was obtained after
several trials with different reaction conditions. In light of these results,
we decided to apply metal catalyzed 5-exe-dig cyclization methodologys.
The exploration to asymmetry synthesis was also investigated in this
thesis.
| en_US |
| DC.subject | 5-exo-dig 合環-Claisen 重排聯繼反應 | zh_TW |
| DC.subject | 萜烯 | zh_TW |
| DC.subject | 5-exe-dig cyclization /Claisen rearrangement | en_US |
| DC.subject | Faveline methyl ether | en_US |
| DC.subject | Terpenes | en_US |
| DC.title | 天然物 Faveline methyl ether 之合成研究 | zh_TW |
| dc.language.iso | zh-TW | zh-TW |
| DC.title | Synthetic studies towards faveline methyl ether | en_US |
| DC.type | 博碩士論文 | zh_TW |
| DC.type | thesis | en_US |
| DC.publisher | National Central University | en_US |