Synthesis of Demethylgorgosterol and Its Stereoisomers
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概要
- 論文の詳細を見る
A stereoselective synthesis of demethylgorgosterol (2) is described. Alkylation at the C-22 position of the steroidal 23-aldehyde (5) was achieved by Claisen rearrangement of the piperidine enamine to give the (22S)-22-aldehyde (10a) predominantly. Compound 10a was transformed to the 22-hydroxymethyl-24-aldehyde mesylate (15a). When the mesylate was treated with potassium t-butoxide, the 22,23-cyclopropyl 24-aldehyde (19a) was obtained in high yield. An isopropyl group was introduced at the C-24 position by means of the Grignard reaction and subsequently the hydroxy group was oxidized to provide the 24-ketone (25a). Wittig reaction of 25a followed by hydroboration and then LiAIH_4 reduction of the mesylate gave 2,which was identical with the natural compound in all physical properties. Three other epimers, the (22R, 23R, 24S)-isomer (32), (22S, 23S, 24R)-isomer (34) and (22S, 23S, 24S)-isomer (35), were prepared by the same procedure. These four isomers can be separated by gas-liquid chromatography on a glass capillary column coated with OV-17.
- 公益社団法人日本薬学会の論文
- 1981-02-25
著者
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石黒 正路
サントリー生物医学研究所
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佐藤 晋
Laboratory Of Chemistry For Natural Products Tokyo Institute Of Technology
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池川 信夫
新潟薬科大学
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池川 信夫
Laboratory Of Chemistry For Natural Products Tokyo Institute Of Technology
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赤岩 明
Laboratory Of Chemistry For Natural Products Tokyo Institute Of Technology
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藤本 善徳
Department of Chemistry, Tokyo Institute of Technology
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藤本 善徳
Department Of Chemistry Tokyo Institute Of Technology
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石黒 正路
Laboratory of Chemistry for Natural Products, Tokyo Institute of Technology
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藤本 善徳
Laboratory of Chemistry for Natural Products, Tokyo Institute of Technology
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Ishiguro Masaji
Department Of Chemistry Tokyo Institute Of Technology:(present Address)suntory Institute For Biomedi
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