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研究生： 周鶴軒
Ho-Hsuan Chou
論文名稱： 建立具亞甲基環戊烷系統的新合環方法及天然物 (±)-Acutifolone A與 (±)-Elisabethin C的合成研究
New Synthetic Methods for Methylenecyclopentane Annulation and Synthetic Studies on (±)-Acutifolone A與 (±)-Elisabethin C
指導教授： 劉行讓
Hsing-Jang Liu
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： 2008
畢業學年度： 96
語文別： 中文
論文頁數： 304
中文關鍵詞： 亞甲基環戊烷 、Acutifolone A 、Elisabethin C
外文關鍵詞： Methylenecyclopentane Annulation, Acutifolone A, Elisabethin C
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    • 摘 要
    本論文內容共分為三個章節：第一章節為天然物 (±)-acutifolone A的型式合成；第二章節為具亞甲基環戊烷 (methylenecyclopentane)雙駢環骨架的新合環方法開發；第三章節則是將開發出來的新合環方法應用於天然物 (±)-elisabethin C的全合成上。

    第一章節：以市售的4-甲基環己酮18為起始物，進行甲氧羰基化 (carbomethoxylation) 後可得α-酯基酮化合物29，藉由兩次的苯基硒化-氧化脫去反應及Michael加成反應，逐次控制位向引進甲基及三甲基矽丁炔基側鍊可得ω-矽炔-α-甲氧羰基環酮化合物27，最後再利用本實驗室開發的碘化鋅環化反應為關鍵步驟及去矽基反應，建構重要的中間產物21，即完成 (±)-acutifolone A (2) 的型式全合成。

    第二章節：以一系列α-腈基環烯酮化合物作為Michael受體，並利用二異丙基胺化鋰 (LDA) 將4-戊烯酸乙酯 (ethyl 4-pentenoate, 80) 去質子化後產生的酯基穩定陰離子作為Michael予體，進行1,4-加成反應，可得相對應之ω-雙鍵-α-腈基環酮化合物，最後在鈀金屬催化誘導下進行分子內環化反應，可完成多鏡像中心取代且具亞甲基環戊烷的新雙駢環骨架。

    第三章節：利用上述第二章節中所合成的順式-雙環[4.3.0]壬環 (cis-bicyclo[4.3.0]nonane) 作為基本骨架，將原先架構上預留之酯基、亞甲基和腈基分別轉換全為順向之甲基、異丁烯基 (isobutenyl) 及丙醯基 (propionyl) 即可完成理論上之天然物 (±)-elisabethin C全合成。目前已完成的工作包括將酯基轉換為甲基 (113→151) 以及將亞甲基轉換為異丁烯基 (151→159)。

    Abstract

    This thesis reports on the formal total synthesis of (±)-acutifolone A, a novel and highly effective ring closure approach to highly substituted bicyclic systems possessing a methylenecyclopentanyl system, and the utility of the aforementioned methodology in a study towards the total synthesis of (±)-elisabethin C.

    Towards the formal total synthesis of (±)-acutifolone A, 4-methyl- cyclo-hexanone (18) was carbomethoxylated and oxidized to furnish β- ketoester 30. Addition of a methyl group in a 1,4-fashion gave β-ketoester 28 which was oxidized to yield enone 19 and subsequently allowed the formation of ketoester 27. Zinc iodide mediated cyclization of ketoester 27 gave bicyclic ketoester 26, the trimethylsilyl moiety of which was removed in the presence of TBAF to furnish ketoester 21, an advance intermediate in a previous total synthesis of (±)-acutifolone A.

    Towards the realization of the aforementioned methodology, 2-cyano- cycloalkenones, readily obtained from commercially available dinitriles, were treated with the lithium enolate of ester 80 to furnish 3-substituted 2-cyanocycloakanones in good to excellent yields. The ring closing process as mediated by palladium acetate in the presence of copper acetate led to the formation of highly substituted bicyclic systems bearing a methylenecyclopentane system and 3 contiguous stereogenic centers.

    Towards the total synthesis of (±)-elisabethin C, the aforementioned methodology was used to rapidly and effectively construct the perhydroindene core bearing 3 of the 5 stereogenic centers found in the targeted natural product (i.e. compound 113). Protection of the ketone moiety found in compound 113 was followed by complete reduction of the remaining ethyl ester and installation of the isopropenyl group to result in bicyclic compound 159. All that remain is to unmask the protected carbonyl group followed by a facial selective alkylation to install the final stereogenic center which will complete the total synthesis of (±)-elisabethin C.

    目 錄 中文摘要…………………………………..…....………..……..…...I 英文摘要………………………………………………………….....…..………...…III 謝誌……………………………………………………………………....…………...V 縮寫對照表……………………………………………………………....…………..VI 目錄…………………………………………………………………………..….…VIII 第一章 天然物 (±)-Acutifolone A的形式合成研究……………………………......1 第一節 緒論…………………………………………………………….....….…....1 第二節 研究構想……………………..………………………….……….......……8 第三節 結果與討論…………………..…………………………..………………11 1.3.1 α-酯基環己酮化合物29的合成……….……...…...……….…….…....…11 1.3.2 α-酯基環己烯酮化合物30的合成…...…...…...…...…...…......................12 1.3.3 兩次Michael加成反應之合成探討..........................................................13 1.3.3 兩次Michael加成反應之合成探討..........................................................13 1.3.4 碘化鋅誘導ω-矽炔-α-甲氧羰基環己酮之環戊烷合成...........................21 1.3.5 去三甲基矽反應合成化合物21...............................................................26 第四節 結論…………………………………………………………….…...…....31 第五節 實驗部分…………………………………………………………..……..32 1.5.1 一般實驗方法............................................................................................26 1.5.2 實驗步驟及光譜資料................................................................................34 第二章 具亞甲基環戊烷系統的新合環反應研究……………...………………….42 第一節 緒論……………………………………………………….….…………..42 2.1.1 引言………...……..…...………………………………………..………..54 2.1.2 以酯類烯醇型式陰離子作為Michael予體之文獻探討…..………...…42 2.1.3 利用醋酸鈀試劑進行分子內環化反應之文獻探討………………....…47 第二節 研究構想…………………………………………….………….....……..53 第三節 結果與討論………………………………………………………………54 2.3.1 α-腈基環酮化合物的製備…………………..…………..……....………..54 2.3.2 α-腈基環烯酮化合物的製備………………….……………….…………58 2.3.3 利用酯基穩定烯醇陰離子進行Michael加成反應的研究.………….…61 2.3.4 ω-雙鍵-α-腈基環酮化合物之環化反應研究………………….…....…...67 2.3.5 環化產物111-125的位向鑑定與光譜分析……...….……….........….…70 2.3.5.1 化合物111與112的鑑定.………......………..................…..…….....70 2.3.5.2 化合物113與114的鑑定.………......……….................…..…….....72 2.3.5.3 化合物115與116的鑑定.………......………..................….…….....74 2.3.5.4 化合物117與118的鑑定.………......……….................……..….....75 2.3.5.5 化合物119、120及121的鑑定......………..........................…….....76 2.3.5.6 化合物122、123及124的鑑定......………..........................…….....80 2.3.5.7 化合物125的鑑定......………............................……………...….....83 第四節 結論…………………………………………………………….…...…....85 第五節 實驗部分…………………………………………………………..……..86 2.5.1 一般實驗方法............................................................................................86 2.5.2 實驗步驟及光譜資料................................................................................86 第三章 天然物 (±)-Elisabethin C的全合成研究……………...……….………....117 第一節 緒論………………………………………………………………..…....117 第二節 研究構想……………………..………………….……….......…………122 第三節 結果與討論…………………..…………………….……………...……123 3.3.1 以α-甲基環己酮作為天然物elisabethine C的起始物…….........……123 3.3.2 以α-腈基環己酮作為天然物elisabethine C的起始物.….....................127 3.3.3 化合物114進行差向異構化反應之探討...............................................129 3.3.4建立縮酮保護基的研究...........................................................................130 3.3.5 將化合物149轉換為化合物150之差向異構化反應探討...................136 3.3.6 酯基還原為甲基之三步驟反應探討......................................................140 3.3.7 環外雙鍵氧化為環氧圜之研究..............................................................145 3.3.8 環氧圜開環為外向醛基之研究..............................................................148 3.3.9 去縮酮化反應之研究探討......................................................................150 3.3.10 去縮酮化後之環氧圜環化反應之研究探討........................................151 第四節 結論………………………………………………………….….…...….153 第五節 實驗部分…………………………………………………………….….155 3.5.1 一般實驗方法..........................................................................................155 3.5.2 實驗步驟及光譜資料..............................................................................155 參考文獻……………………………………………………………..…..…….…...167 附錄一 化合物之X-射線繞射實驗數據…………………………………....…….174 附錄二 化合物之NMR (1H NMR、13C NMR、DEPT) 光譜圖…………..…...…..252

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