不對稱全合成(-)-Isooncinotine與擬全合成Zoapatanols－結合環閉合置換反應和甲酸還原反應

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鄭秀宜(Hsiu-yi Cheng) 查詢紙本館藏

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論文名稱

不對稱全合成(-)-Isooncinotine與擬全合成Zoapatanols－結合環閉合置換反應和甲酸還原反應
(Asymmetric Synthesis of (-)-Isooncinotine and Formal Syntheses of Zoapatanols by Ring-Closing Metathesis/Regioselective Formate Reduction)

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摘要(中)

此論文有兩篇主題，首先是結合環閉合置換反應（ring closing metathesis）和位置選擇性甲酸還原反應（regioselective formate reduction）得到環外烯烴化合物的方法。開發以氯化烯丙基鈀（II）二聚物（allylpalldium chloride dimer）、二-三級丁基 2-聯苯基膦（di-tert-butyl 2-biphenylphosphine）、甲酸和三乙胺在N,N-二甲基甲醯胺溶劑下還原烯丙基酯（allylic acetate），可以有很好的區域選擇性和高產率得到環外烯烴（exocyclic olefins）結構，並利用此方法完成(-)-zoapatanol擬全合成（formal synthesis）。此不對稱合成以 (L)-蘋果酸（L-malic acid）衍生之內酯為起始物，藉由螯合控制（chelation control）進行親核性醯基加成反應（nucleophilic acyl addition）後得到zoapatanols結構中相鄰的兩個不對稱中心並且有很好的非鏡像選擇性。氧化、烴烯化、丙烯化、環閉合置換反應以及鈀金屬催化甲酸還原反應後得到關鍵中間物達成此擬全合成。
第二個主題是不對稱合成(-)-isooncinotine。利用(1S)-樟腦磺酸將外消旋的2-六氫吡啶基乙醇（2-piperidineethanol）作拆分（resolution）後，得到單一光學異構物作為起始物。然後作醯化、Michael加成和以三氫化鋁還原得到spermidine的骨架。環閉合置換反應形成具有22員環的內醯胺。我們發現以四氫化鋁鋰還原時會進行Michael加成的逆反應，因此深入研究四氫化鋁鋰或三氫化鋁還原β位置上具有醯胺或胺集團丙腈之差異。

摘要(英)

There are two topics in the thesis. The first is formal syntheses of zoapatanols by ring-closing metathesis/regioselective formate reduction.
The combination of ring-closing metathesis and regioselective formate reduction is an effective strategy for the synthesis of cyclic compounds with exo olefins. Reduction of allylic acetates, formed by ring-closing metathesis, using allylpalladium chloride dimer, di-tert-butyl 2-biphenyl-phosphine, and formic acid/ triethylamine in DMF gives the exo-cyclic olefins with excellent regioselectivity and high yields under a mild condition. Synthetic application to prepare zoapatanols is accomplishing. The key vicinal stereocenters in zoapatanol were constructed from the L-malic acid dericed lactone by the nucleophilic acyl addition with excellent diastereoselectivities. Then the oxidation, Olefination, subtle allylation, RCM and Pd-formate reduction to get the key intermediums。
The second is asymmetric synthesis of (‒)-isooncinotine. The asymmetric total synthesis of the macrocyclic spermidine alkaloid isooncinotine, was completed by efficient RCM from resolution of 2-piperidineethanol as a starting material. Michael addition, amidations, and aluminum hydride reduction were applied to form the moiety of spermidine. Retro-Michael addition was observed when β-amido- and β-amino-propionitriles were reduced by LAH. The effects of LAH versus AlH3 were discussed.

關鍵字(中)

★ 還閉合置換反應
★ 甲酸還原反應

關鍵字(英)

★ RCM
★ Zoapatanol
★ Isooncinotine
★ formate reduction
★ ring-closing metathesis

論文目次

中文論文摘要..............................................I
Abstract ..............................................III
致謝......................................................V
總目錄................................................VII
圖目錄.................................................XI
流程圖目錄.........................................XIII
表目錄.................................................XV
附圖目錄.........................................XVII
第一章序論...............................................1
1-1 研究之背景與目的......................................1
1-2 環閉合置換後進行衍生的實例............................2
1-3 提出的解決方法........................................4
1-4 環閉合置換反應（RCM）的介紹...........................5
1-5 鈀金屬催化甲酸還原反應的介紹..........................7
1-6 最近國內外研究........................................9
第二章鈀金屬催化甲酸還原反應於氮雜環化合物的研究與討論..11
2-1 逆合成分析...........................................11
2-2 化合物 4 的製備......................................12
2-3化合物 5 的製備.......................................13
2-4 鈀金屬催化甲酸還原反應前軀物 2 的製備................14
2-5 鈀金屬催化甲酸還原反應的條件.........................15
2-6 環內烯烴（endocyclic-olefin）化合物結構的確定........23
2-7 應用.................................................24
第三章鈀金屬催化甲酸還原反應於氧雜環化合物的研究與討論..27
3-1 前言.................................................27
3-2 模型化合物的製備.....................................27
3-3 鈀金屬催化甲酸還原反應的條件.........................28
3-4 Zoapatanol的介紹....................................30
3-5 (+)-zoapatanol的合成................................31
3-6 合成方法的構思.......................................36
3-7 化合物 20 的製備.....................................38
3-8 立體中心的確定.......................................39
3-9 化合物30 的製備......................................41
3-10 雙醇化合物的製備....................................42
3-11 環閉合置換反應前驅物的製備..........................43
3-12 Zoapatanol的擬全合成（formal syntheses）............46
3-13 化合物53開環之探討..................................48
第四章不對稱合成(-)-isooncinotine.......................49
4-1 研究背景.............................................49
4-2 不對稱合成(-)-isooncinotine的實例....................50
4-3逆合成分析............................................51
4-4 光學純度的確定.......................................52
4-5 化合物62的製備.......................................54
4-6 環閉合置換反應前驅物的製備...........................55
4-7 還原反應之副產物結構的確定...........................57
4-8 β位置上具有醯胺或胺集團丙腈的還原反應探討...........58
4-9 經由環閉合置換反應合成(-)-isooncinotine..............60
第五章結論..............................................63
第六章實驗步驟..........................................65
6-1 溶媒及處理過程.......................................65
6-2 實驗器材及光譜儀器...................................65
6-3 實驗步驟.............................................67
第七章參考文獻.........................................123

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指導教授

侯敦仁(Duen-Ren Hou)

審核日期

2011-8-26

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