29 4-Methylene-cyclohex-Z-enoneをMichael acceptorとする環化反応を用いた2,3のセスキテルペンの合成研究
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概要
- 論文の詳細を見る
Double Michael reaction of 4-methylene-3-methyl-cyclohex-2-enone as a Michael acceptor and dimethyl 3-oxoglutarate as a Michael doner in the presence of potassium fluoride in dimethyl sulphoxide gave 6,8-di(methoxycarbonyl)-2,7-dioxo-9-methyl-cis-decalin stereoselectively. 4-Methylene-3,5-dimethyl-cyclohex-2-enone gave two 6,8-di(methoxycarbonyl)-4,9-dimethyl-2,7-dioxo-cisdecalins in the same manner, the structures of which were confirmed by X-ray crystallographic analysis. Application of the procedure on 4-methylene-2,3-dimethyl-cyclo-hex-2-enone gave 6,8-di(methoxycarbonyl)-1,9-dimethy1-2,7-dioxo-cis-decalin, which was transformed into the key-compound for synthesis of furanoeremophilane, eremophilenolide, and fukinone, providing a formal synthesis of these sesquiterpenes. Next, the synthesis of (±)-occidentalol was completed in a stereoselective manner, starting from one of two stereoisomeric 4,9-dimethyl-cis-decalin mentioned above.
- 天然有機化合物討論会の論文
- 1979-09-20
著者
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片川 純一
Faculty of Pharmaceutical Sciences, Setsunan University
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入江 寛
長崎大薬
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入江 寛
長崎大学薬学部
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多賀 徹
京大・薬
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水野 行雄
Faculty of Pharmaceutical Sciences, Kyoto University
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入江 寛
京大・薬
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水野 行雄
京大・薬
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片川 純一
京大・薬
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伏見 環
京大・薬
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大崎 健次
京大・薬
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水野 行雄
Faculty Of Pharmaceutical Sciences Kyoto University
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片川 純一
Faculty Of Pharmaceutical Sciences Setsunan University
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大崎 健次
Faculty of Pharmaceutial Sciences, Kyoto University
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