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研究生:李政霖
研究生(外文):Jeng-Lin Lee
論文名稱:Rollicosin全合成之探討
論文名稱(外文):Studies On Total Synthesis Of Rollicosin
指導教授:吳明忠吳明忠引用關係
指導教授(外文):Ming-Jung Wu
學位類別:碩士
校院名稱:高雄醫學大學
系所名稱:天然藥物研究所
學門:醫藥衛生學門
學類:藥學學類
論文種類:學術論文
論文出版年:2001
畢業學年度:89
語文別:中文
論文頁數:71
中文關鍵詞:細胞毒性番荔枝科番荔枝科乙醯生合成物
外文關鍵詞:cytotoxicityAnnonaceaeAcetogenin
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  • 下載下載:3
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中文摘要
Rollicosin (2) 是由Rollinia mucosa Bill 所分離出,並展現了對Hep 2, 2, 15 腫瘤細胞的優越活性,因此我們設計了一個藉由Pd催化連接內酯化物43b及乙烯碘化物44b的合成方法,內酯化物43b是由5-己炔-1-醇為起始物的六個步驟,經由TMSCl保護末端炔,以PCC氧化醇形成醛,醛基經由溴鎂乙烯加成,Claisen 重排反應得到γ,δ -不飽和酯,不對稱雙醇化,去矽烷反應,可得到內酯物43b,總產率為2 %。
碘化合物55b是由起始物5-乙烯-1-醇,總產率為14 %,合成步驟包括,以DHP保護醇基,以AD-mix-α進行不對稱雙醇化,將雙醇基環氧化,以碘化鈉進行環氧基之開環反應,以TBDMSCl保護二級醇,以PPTS去THP保護形成醇基,PCC氧化一級醇形成醛, 藉二氯化鉻及碘仿將醛基形成乙烯碘,將化合物43b及55b偶合的反應仍在研究中。

英文摘要
Rollicosin (2) was isolated from Rollinia mucosa Bill and shown potent inhibition propecty against human tumor cell line Hep2, 2, 15. A convergent synthesis of rollicosin was designed by palladium catalyzed coupling reaction of lactone 43b and vinyl iodide 44b.
Lactone 43b was prepared starting from 5-hexyn-1-ol in six steps including protection of the terminal acetylene, oxidation of the alcohol, vinyl magnesium bromide addition to the aldehyde, ortho-ester Claisen rearrgangement to give the,γ,δ-unsaturated ester, asymmetric dihydroxylation to give a lactone and desilylation. The overall yield is 2 % . Compound 44b could be prepared by alkylation of 56 with iodide 55b. Iodide 55b was synthesized starting from 5-hexen-1-ol in eight steps in 14% overall yield. This synthesis included protection of hydroxyl group, asymmetric dihydroxylation using AD-mix-α, convertion of the diol to expoxide, expoxide openning by the treatment of sodium iodide, protection of the secondary alcohol with TBDMSCl, removal of the protecting group on the primary hydroxyl group, and following the PCC oxidation to the aldehyde, finally convertion of the aldehyde to vinyl iodide. Conversion of 43b and 55b to rollicosin is under investigation.

目錄
英文摘要
中文摘要
壹.緒論------------------------------------------------------------------1
1.1引言-------------------------------------------------------------1
1.2生物活性------------------------------------------------------- 2
貳.研究動機------------------------------------------------------------ 6
參.論文回顧-------------------------------------------------------------7
肆.合成策略與逆合成分析-----------------------------------------18
伍.結果-----------------------------------------------------------------25
陸.結論-----------------------------------------------------------------37
柒.實驗設備及試藥部分--------------------------------------------40
捌.化合物之制備過程-----------------------------------------------43
玖.參考文獻-----------------------------------------------------------71

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