- 學位論文
天然物 Faveline methyl ether 之合成研究
Synthetic studies towards faveline methyl ether
摘要
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。
並列摘要
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.
參考文獻
延伸閱讀
- 江喬華（2008）。天然物(－)-Bakkenolide III之全合成與Laurenene、Ottelione A之合成研究〔博士論文，國立清華大學〕。華藝線上圖書館。https://doi.org/10.6843/NTHU.2008.00331
- 李弘毅（2011）。天然物 Ottelione A之合成研究與 Peribysin E 之全合成〔博士論文，國立清華大學〕。華藝線上圖書館。https://doi.org/10.6843/NTHU.2011.00081
- 陳政輝（2008）。天然物Ottelione A之全合成研究〔博士論文，國立清華大學〕。華藝線上圖書館。https://doi.org/10.6843/NTHU.2008.00121
- 虞正平（2017）。Synthetic Study toward Pseudouridine〔碩士論文，國立臺灣師範大學〕。華藝線上圖書館。https://doi.org/10.6345/NTNU202203512
- 張莉德（2004）。Synthetic Studies on Optically Pure N-Substituted Morphine Derivatives with ACNO Skelton〔碩士論文，國立臺灣大學〕。華藝線上圖書館。https://doi.org/10.6342/NTU.2004.01889