Total Synthesis of the Lycopodium Alkaloid dl-Serratinine
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概要
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Total synthesis of dl-serratinine (1 : dl-form) has been completed as follows. The Wittig reaction of the aldehyde (6) with diethylcyanomethylphosphonate gave the conju-gated nitrile (7) which was subjected to hydrogenation, followed by NaBH_4-CoCl_2 reduction to provide the primary amine (10). Treatment of (10) with NCS and Cu_2Cl_2 gave the aziridine A (11) and the aziridine B (12). The aziridine A was derived to the aziridinium salt (14) via the primary alcohol (13) and its tosylate, and the reaction of 14 with AcOK afforded the triacetate (15). Hydrolysis of 15,followed by oxidation with Jones'reagent gave the triketone (18). Finally, reduction of 18 with NaBH_4 afforded dl-serrat-inine (1 : dl-form) and dl-8-episerratinine (19 : dl-form).
- 公益社団法人日本薬学会の論文
- 1975-07-25
著者
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原山 尚
Faculty of Pharmaceutical Sciences, Chiba University
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犬伏 康夫
Faculty of Pharmaceutical Sciences, Kyoto University
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原山 尚
Faculty Of Pharmaceutical Sciences Kyoto University
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犬伏 康夫
Faculty Of Pharmaceutical Sciences Kyoto University
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沖 正信
Faculty Of Pharmaceutical Sciences Kyoto University
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大谷 光昭
Shionogi Research Laboratories Shionogi & Co. Ltd.
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大谷 光昭
Faculty of Pharmaceutical Sciences, Kyoto University
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