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Structural Studies of Tetranortriterpenoids from the Congolese species of Entandrophragma angolense And Efficient Short Step Synthesis of Corey’s Tamiflu Intermediate
http://hdl.handle.net/10232/4878
http://hdl.handle.net/10232/4878e892d6e0-3cde-4c24-946d-29624c93c7c3
| 名前 / ファイル | ライセンス | アクション |
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rikouken288.pdf (138.8 kB)
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diss_riko288_Nsiama_Tienabe_Kipassa_20080325.pdf (3.3 MB)
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| Item type | 学位論文 / Thesis or Dissertation(1) | |||||
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| 公開日 | 2015-02-18 | |||||
| タイトル | ||||||
| タイトル | Structural Studies of Tetranortriterpenoids from the Congolese species of Entandrophragma angolense And Efficient Short Step Synthesis of Corey’s Tamiflu Intermediate | |||||
| タイトル言語 | en | |||||
| 著者 |
Nsiama Tienabe Kipassa
× Nsiama Tienabe Kipassa |
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| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_db06 | |||||
| 資源タイプ | doctoral thesis | |||||
| アクセス権 | ||||||
| アクセス権 | open access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_abf2 | |||||
| 要約 | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | 理工学研究科博士論文(理学) ; 学位取得日: 平成20年3月25日 | |||||
| 内容記述言語 | ja | |||||
| 要約 | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | This dissertation comprises two parts, one is the chemistry of natural products dealing with the isolation and structure elucidation of limonoids and the second part is synthetic organic chemistry dealing with the use of a stereoselective based-catalyzed Diels-Alder reaction for the synthesis of small biologically active compound ingredient. Structural Studies of Tetranortriterpenoids from the Congolese species of Entandrophragma angolense The extracts of E. angolense, a Meliaceae plant used in African folk medicine against malaria, displayed considerable antifeedant activity against Spodotera insects. Thus, the plant was selected for further fractionation of its extracts. The fractionation of the extracts has been carried out using chromatographic methods and resulted to the isolation of twenty-three compounds. The structure elucidation of these compounds was performed by spectroscopic methods including mass spectrometry, 1D and 2D NMR. Two compounds are not limonoids and the remaining ones are limonoids and could be classified as protolimonoid, gedunin, andirobin and phragmalin compound-types. Sixteen compounds have been found to be new rings and the five known compounds isolated have been identified as methyl angolensante, methyl 6-acetoxyangolensante, secomahoganin, 3β-hydroxy-3-deoxycarapin and xyloccensin K. Efficient Short Step Synthesis of Corey’s Tamiflu Intermediate Catalysts have been used to facilitate the Diels-Alder reaction and almost catalysts developed are Lewis acids. Our lab developed a unique base-catalyzed diastereoselective Diels-Alder reaction of pyridone derivative as diene and electron deficient dienophiles. The unique poly-functionalized bicyclolactam obtained from the reaction between N-nosyl-3-hydroxy-2-pyridone and ethyl acrylate has been used as building block for the synthesis of Corey’s Tamiflu intermediate. This synthesis route is short and the production of different intermediates is simple. Only four chemical transformations and three purification steps are required to obtain the targeted compound, equivalent to the Tamiflu intermediate from the Diels-Alder adduct. |
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| 内容記述言語 | en | |||||
| 作成日 | ||||||
| 日付 | 2008-03-25 | |||||
| 日付タイプ | Issued | |||||
| 出版タイプ | ||||||
| 出版タイプ | VoR | |||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
| NDC | ||||||
| 主題Scheme | NDC | |||||
| 主題 | 500 | |||||
| ファイル（説明） | ||||||
| 内容記述 | 学位論文の要旨, 学位論文本文 | |||||
| 公開者・出版者 | ||||||
| 出版者 | 鹿児島大学 | |||||
| 出版者言語 | ja | |||||
| 公開者・出版者 | ||||||
| 出版者 | Kagoshima University | |||||
| 出版者言語 | en | |||||
| 学位名 | ||||||
| 学位名の言語 | ja | |||||
| 学位名 | 博士(理学) | |||||
| 学位名 | ||||||
| 学位名の言語 | en | |||||
| 学位名 | Doctor of Philosophy in Science | |||||
| 学位授与機関名 | ||||||
| 学位授与機関識別子Scheme | kakenhi | |||||
| 学位授与機関識別子 | 17701 | |||||
| 学位授与機関名の言語 | ja | |||||
| 学位授与機関名 | 鹿児島大学 | |||||
| 学位授与年月日 | ||||||
| 学位授与年月日 | 2008-03-25 | |||||
| 学位授与番号 | ||||||
| 学位授与番号 | 甲理工研第288号 | |||||
