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In order to create the polymer, we synthesize several natural compounds as biologically active monomers. An efficient synthesis of highly substituted a -arylnaphthalene analogs has been developed utilizing Lewis acid-promoted regiocontrolled benzannulation of aryl(aryl\u0027)-2, 2-dichlorocyclopropylmethanols (aryl1 aryl’ ; abbreviated as AACMs). Both AACM diastereomers were easily prepared via highly stereoselective addition (\u003e 95:5) of ArLi to gem-dichlorocyclopnopropyl atyl\u0027 ketones. The choice of Lewis acids determined the cyclization regioselectivity of the present benzannulation. TiCl4 and SnCl4 used the chelation pathway, whereas silyl triflates used a non-chelation pathway to give unsymmetrically substituted regioisomeric a -arylnaphthalenes in 40-91% yields with moderate to excellent regioselectivity(TiCl4 or SnCl4; \u003e99/1-3/1, TBDMSOTf; \u003e1/99-1/4). 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15-3-21 : 生理活性繊維を目指した光学活性有機化合物(モノマーおよびポリマー)の合成
http://hdl.handle.net/10091/13411
http://hdl.handle.net/10091/13411f09f4c48-b9c0-4273-a571-fad96f67bf85
名前 / ファイル | ライセンス | アクション |
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AFSTT11-317.pdf (544.1 kB)
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Item type | 研究報告書 / Research Paper(1) | |||||
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公開日 | 2011-12-05 | |||||
タイトル | ||||||
言語 | ja | |||||
タイトル | 15-3-21 : 生理活性繊維を目指した光学活性有機化合物(モノマーおよびポリマー)の合成 | |||||
言語 | ||||||
言語 | jpn | |||||
資源タイプ | ||||||
資源 | http://purl.org/coar/resource_type/c_18ws | |||||
タイプ | research report | |||||
その他(別言語等)のタイトル | ||||||
その他のタイトル | 高次機能創出加工 | |||||
著者 |
西井, 良典
× 西井, 良典 |
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信州大学研究者総覧へのリンク | ||||||
氏名 | 西井, 良典 | |||||
URL | http://soar-rd.shinshu-u.ac.jp/profile/ja.yeSUjFkV.html | |||||
出版者 | ||||||
出版者 | 信州大学繊維学部 | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | 先進ファイバー工学研究教育拠点研究成果報告書 11: 86-86(2005) | |||||
書誌情報 |
先進ファイバー工学研究教育拠点研究成果報告書 巻 11, p. 86-86, 発行日 2005-03-31 |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | We are going to apply optically active organic compounds having biological activity, for example, antiviral, anti-HIV, anti-PAF, anti-malarial, anti-fungal, anti-tumor activiry, to biologically active textile. In order to create the polymer, we synthesize several natural compounds as biologically active monomers. An efficient synthesis of highly substituted a -arylnaphthalene analogs has been developed utilizing Lewis acid-promoted regiocontrolled benzannulation of aryl(aryl')-2, 2-dichlorocyclopropylmethanols (aryl1 aryl’ ; abbreviated as AACMs). Both AACM diastereomers were easily prepared via highly stereoselective addition (> 95:5) of ArLi to gem-dichlorocyclopnopropyl atyl' ketones. The choice of Lewis acids determined the cyclization regioselectivity of the present benzannulation. TiCl4 and SnCl4 used the chelation pathway, whereas silyl triflates used a non-chelation pathway to give unsymmetrically substituted regioisomeric a -arylnaphthalenes in 40-91% yields with moderate to excellent regioselectivity(TiCl4 or SnCl4; >99/1-3/1, TBDMSOTf; >1/99-1/4). Thus, the a -Afyl or a -aryl' moiety(accessory aryl group) was alternatively introduced to a -arylnaphthalenes by choosing either the order of the reaction sequences or the appropriate catalyst. Application of the present method to the total synthesis for unsymmetrically substituted natural lignan lactones, justicidin B, retrojusticidin B, dehydrodesoxypodophyllotoxin, and a related analog, 5’-methoxyrettvchinensin, was demonstrated. Lignan retrolactones (retrojusticidin B and 5’-methoxyretrochinensin) were synthesized by the conventional lactonization of the diol precursor, whereas a novel Bu2SnO-mediated monoacylation method was applied to the synthesis of normal lignan lactones (justicidin B and dehydrodesoxypodophyllotoxin). | |||||
資源タイプ(コンテンツの種類) | ||||||
内容記述タイプ | Other | |||||
内容記述 | Article | |||||
書誌レコードID | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AA1200368X | |||||
出版タイプ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 |