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研究生： 楊以仁
Yi-Jen Yang
論文名稱： N,N-二異丙基-10-樟腦磺醯胺衍生之具掌性1,3-氧硫環戊-5-酮在不對稱合成上的應用
Applications of N,N-Diisopropyl 10-camphorsulfonamide Derived Chiral 1,3-Oxathiolan-5-one in Asymmetric Synthesis
指導教授： 汪炳鈞
Biing-Jiun Uang
口試委員:
學位類別： 博士
Doctor
系所名稱： 理學院 - 化學系
Department of Chemistry
論文出版年： 2005
畢業學年度： 93
語文別： 中文
論文頁數： 326
中文關鍵詞： 掌性輔助基 、N,N-二異丙基-10-樟腦磺醯胺 、1,3-氧硫環戊-5-酮 、不對稱烷基化反應 、不對稱醛醇反應 、不對稱亞胺醛醇反應
外文關鍵詞： chiral auxiliary, N,N-diisopropyl-10-camphor sulfonamide, 1,3-oxathiolan-5-one, asymmetric alkylation, asymmetric aldol reaction, asymmetric imine-aldol reaction, daunosamine, staurosporine
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    • 本論文概分為二部份，第一部份是利用N,N-二異丙基-10-樟腦磺醯胺(N,N-diisopropyl-10-camphorsulfonamide) 22作為掌性輔助基，經活化為二甲基縮酮25後，與硫醇乙酸縮合形成1,3-氧硫環戊-5-酮28，應用於不對稱烷基化反應(alkylation)、不對稱醛醇反應(aldol reaction)和不對稱亞胺醛醇反應(imine-aldol reaction)，以合成具光學活性之硫醇乙酸衍生物。

    內酯縮酮化合物28進行不對稱烷基化反應，僅得到單一烷基化產物29；將29d在酸性條件下進行醇解反應，可得3-苯基-2-硫醇丙酸甲酯(R)-56a，其光學純度仍保持100 %。內酯縮酮化合物29a、29d分別進行不對稱烷基化反應，亦得到單一烷基化產物55；分別將55d、55e在鹼性條件下進行醇解反應，可分別得2-甲基-3-苯基-2-硫醇丙酸甲酯(R)-56b與(S)-56b，其光學純度仍保持100 %。

    內酯縮酮化合物28與醛類化合物進行不對稱醛醇反應，選擇性不甚理想。當在芳香醛與共軛醛的反應中加入氯化鋰可有效增加anti的產物71；而加入六甲基磷醯胺則可增加syn的產物72，但在酯肪醛中的異丁醛與丙醛可得到單一產物72。

    使用催化量的對甲苯磺酸吡啶鹽(PPTS)，在微酸性的條件下促使對甲苯磺醯胺與醛類化合物進行脫水反應，得到對甲苯磺醯亞胺75，且可應用於合成共軛醛亞胺。內酯縮酮化合物28與亞胺化合物75進行不對稱亞胺醛醇反應，具有中等的選擇性。當在反應中加入氯化鋰可有效增加syn的產物89；而加入六甲基磷醯胺亦可增加anti的產物90，其中在芳香醛亞胺的結果幾乎為單一產物90。

    第二部份是利用亞胺醛醇反應的產物，應用於抗生素去氧胺基醣daunosamine與staurosporine的不對稱合成。從不具光學活性的硫醇乙酸開始，使用樟腦磺醯胺22為掌性輔助基生成具掌性之內酯縮酮化合物28，再經由不對稱亞胺醛醇反應誘導C3掌性中心的生成、不對稱順式羥基化反應建立C4與C5的掌性中心、還原反應、酸性異構化反應和去對甲苯磺醯保護基，經由六個步驟合成D-daunosamine的總產率為20 %；staurosporine的胺基醣部份177則由合成D-daunosamine的中間物α-D-118開始，再經由甲基化反應、縮醛水解、還原反應和氧化反應，經由四個步驟合成。

    Part I: Applications in asymmetric alkylation, asymmetric aldol reaction and asymmetric imine-aldol reaction of a novel chiral 1,3-oxathiolan-5-one 28, derived from chiral auxiliary N,N-diisopropyl-10-camphor sulfonamide 22 through dimethoxy ketal 25, are studied.

    In the asymmetric alkylation reactions using 1,3-oxathiolan-5-one 28 furnished the alkylation product 29 as a single isomer. Removal of the auxiliary from compound 29d via methanolysis under acidic conditions provided methyl 3-phenyl2-sulfanyl propanoate (R)-56a in 100% optical purity. Similarly when 1,3-oxatiolan-5-one derivatives 29a and 29d were subjected to further alkylation gave compounds 55 as the only products. Basic methanolysis of the compounds 55d and 55e gave methyl-2-methyl-3-phenyl-2-sulfanyl propanoate: (R)-56b, (S)-56b in 100% optical purity.

    1,3-oxathiolan-5-one 28 with aldehydes in asymmetric aldol reaction gave moderate selectivities. In the cases of aromatic or conjugated aldehydes, when an additive LiCl was added, anti products 71 were formed in major; while addition of HMPA saw the increase in syn products 72. In contrast, isobutyraldehyde and propionaldehyde offered single isomers.

    Asymmetric aldol reaction was extended to asymmetric imine-aldol reaction. Initially, N-tosylaldimines 75 were prepared from aldehydes and p-toluenesulfanamide under the catalytic influence of PPTS in benzene. Moderate selectivities were obtained similar to the asymmetric aldol reactions, on treating N-tosylaldimines with 1,3-oxathiolan-5-one 28. Additives provided an increase in either syn-products 89 (LiCl) or anti-products 90 (HMPA).

    Part II: Application of asymmetric imine-aldol reaction in the synthesis of antibiotic deoxyaminosugar – daunosamine and staurosporine is studied. Initiating our strategy from racemic starting material, thioglycolic acid with camphor sulfonamide 22 as chiral auxiliary provided daunosamine in 6 steps (namely asymmetric aldol reaction with compound 28 to induce chirality at C3 position, asymmetric cis-dihydroxylation to create C4 and C5 chiral centers followed by reduction, acid catalyzed isomerization and deprotection) and 20% overall yield. Compound α-D-118 from the intermediary step in the synthesis of daunosamine was used in the preparation of compound 177, an acyclic form of amino sugar, a potential intermediate for the efficient synthesis of staurosporine. The synthesis of compound 177 could be accomplished in 4 steps from compound α-D-118 which can be cyclized to get amino sugar part of staurosporine and further complete the total synthesis.

    中文摘要...................................................i 英文摘要.................................................iii 謝誌.......................................................v 目錄.....................................................vii 圖目錄..................................................xiii 表目錄..................................................xvii 縮寫對照表...............................................xix 第一章 緒論...............................................1 第一節 具光學活性化合物製備的方法........................3 第二節 樟腦為掌性輔助基在不對稱合成上的應用..............6 第三節 研究構思.........................................12 第二章 合成樟腦磺醯胺為掌性輔助基的1,3-氧硫環戊-5-酮及其在不對稱烷基化反應的研究....................................15 第一節 文獻回顧.........................................16 第二節 具掌性1,3-氧硫環戊-5-酮的合成....................20 第三節 不對稱烷基化反應的研究結果.......................27 第四節 結論.............................................39 第三章 掌性1,3-氧硫環戊-5-酮在不對稱醛醇(aldol)反應與不對稱亞胺醛醇(imine-aldol)反應的探討...........................41 第一節 不對稱醛醇反應的研究結果.........................42 第二節 亞胺的製備方法...................................51 第三節 不對稱亞胺醛醇(imine-aldol)反應的研究結果........57 第四節 結論.............................................64 第四章 掌性1,3-氧硫環戊-5-酮應用於合成具光學活性去氧胺基醣的研究....................................................65 第一節 Daunosamine的歷史背景............................66 第二節 Daunosamine的研究結果............................70 第三節 Staurosporine的文獻回顧..........................87 第四節 Staurosporine的合成研究..........................96 第五節 結論............................................102 第五章 實驗部份.........................................103 第一節 一般實驗方法....................................103 第二節 合成樟腦磺醯胺為掌性輔助基的1,3-氧硫環戊-5-酮及其在不對稱烷基化反應的研究之實驗步驟與光譜資料...............105 5.2.01 化合物28和54的合成............................105 5.2.02 化合物29a的合成...............................107 5.2.03 化合物29b的合成...............................109 5.2.04 化合物29c的合成...............................110 5.2.05 化合物29d的合成...............................111 5.2.06 化合物55a的合成...............................112 5.2.07 化合物55b的合成...............................114 5.2.08 化合物55c的合成...............................115 5.2.09 化合物55d的合成...............................117 5.2.10 化合物55e的合成...............................118 5.2.11 化合物57的合成................................119 5.2.12 化合物58的合成................................120 5.2.13 化合物56a的合成...............................122 5.2.14 化合物(R)-56a的合成...........................123 5.2.15 化合物59的合成................................123 5.2.16 化合物60的合成................................124 5.2.17 化合物56b的合成...............................125 5.2.18 化合物(R)-56b的合成...........................126 5.2.19 化合物(S)-56b的合成...........................127 第三節 掌性1,3-氧硫環戊-5-酮在不對稱醛醇(aldol)反應與不對稱亞胺醛醇(imine-aldol)反應的探討之實驗步驟與光譜資料....129 5.3.01 化合物71a與72a的合成..........................129 5.3.02 化合物71b與72b的合成..........................133 5.3.03 化合物71c與72c的合成..........................136 5.3.04 化合物71d與72d的合成..........................139 5.3.05 化合物71e與72e的合成..........................142 5.3.06 化合物72f的合成...............................144 5.3.07 化合物72g的合成...............................144 5.3.08 化合物75a的合成...............................146 5.3.09 化合物75b的合成...............................147 5.3.10 化合物75c的合成...............................148 5.3.11 化合物75d的合成...............................148 5.3.12 化合物75e的合成...............................149 5.3.13 化合物75f的合成...............................150 5.3.14 化合物75g的合成...............................151 5.3.15 化合物75h的合成...............................152 5.3.16 化合物75i的合成...............................153 5.3.17 化合物75j的合成...............................154 5.3.18 化合物89a與90a的合成..........................155 5.3.19 化合物89d與90d的合成..........................161 5.3.20 化合物89e與90e的合成..........................164 5.3.21 化合物89f與90f的合成..........................168 第四節 掌性1,3-氧硫環戊-5-酮應用於合成具光學活性去氧胺基醣的研究之實驗步驟與光譜資料...............................172 5.4.01 化合物112的合成...............................172 5.4.02 化合物115的合成...............................173 5.4.03 化合物116的合成...............................174 5.4.04 化合物117的合成...............................176 5.4.05 化合物α-D-118的合成..........................177 5.4.06 化合物β-L-119的合成..........................179 5.4.07 化合物α-L-118的合成..........................180 5.4.08 甲基 α-D式daunosaminide的合成................181 5.4.09 化合物171的合成...............................182 5.4.10 化合物174的合成...............................184 5.4.11 化合物175的合成...............................185 5.4.12 化合物176的合成...............................186 5.4.13 化合物177的合成...............................187 參考文獻.................................................189 附錄一 化合物28、29a、55d、55e與89a的X-ray單晶繞射數據..201 附錄二 化合物29c與29d的nOe實驗光譜圖....................207 附錄三 化合物的氫核磁共振光譜圖.........................215

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