11 Eudesmanolideの骨格転位に関する反応経路の解析
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概要
- 論文の詳細を見る
Eudesmanolides (1, 17) was subjected to a novel skeletal-cyclization rearrangement to trimethylethanoadamantanone (2) using hot phosphoryl chloride. When the reaction product was treated with hot aqueous sodium hydroxide, new epoxytricycloeudesmanone (5) and tricycloeudesmendiones (6, 7) were isolated in addition to the epoxy ketone (4). The absolute stereostructures of 5, 6 and 7 were determined by spectrometric and X-ray crystallographic methods. Tricycloeudesmenones (8, 9) as the main product in the aforementioned reaction were neatly separated through the reoxidation of their alcohol derivatives (10, 11), and well characterized by correlating 8 and 9 with 4, 5, 6, and 7. A unique structure of the byproduct (12) obtained besides 10 and 11 on LiAlH_4 reduction of 8 and 9 was also elucidated. The proposed reaction pathway from 1 to 2 through carboxyeudesmene intermediates and the key intermediate tricycloeudesmenones (8, 9) was rationalized on the basis of acid catalized rearrangement experiments and the force field calculation for possible candidate intermediates (8, 9 to 2) created by using a computer technique.
- 天然有機化合物討論会の論文
- 1980-09-10
著者
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飯高 洋一
東大・薬
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飯高 洋一
Nishi-tokyo Science University
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堀 均
Pharmaceutical Institute School Of Medicine Keio University
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柴田 徹一
慶應義塾大学薬化学研究所
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飯高 洋一
Faculty Of Pharmaceutical Sciences University Of Tokyo
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飯高 洋一
西東京科学大学理工学部
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川又 健
Pharmaceutical Institute, School of Medicine, Keio University
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大坂 哲司
Pharmaceutical Institute, School of Medicine, Keio University
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稲山 誠一
Institute Of Oriental Medical Sciences
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稲山 誠一
慶應義塾大学医学部薬化学研究所
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清水 信子
Pharmaceutical Institute School Of Medicine Keio University
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稲山 誠一
慶大・医・薬化研
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堀 均
慶大・医・薬化研
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大坂 哲司
慶大・医・薬化研
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清水 信子
慶大・医・薬化研
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柴田 徹一
慶大・医・薬化研
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川又 健
慶大・医・薬化研
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川又 健
Pharmaceutical Institute School Of Medicine Keio University
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大坂 哲司
Pharmaceutical Institute School Of Medicine Keio University
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