47 大環状スペルミジンアルカロイドの新全合成
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概要
- 論文の詳細を見る
Total synthesis of codonocarpine (5), a 24-membered ring spermidine dilactam alkaloid isolated from Codonocarpus australis by Doskotch et al., has been accomplished. The key step is aminolysis of the compound (13) with spermidine (4). Codonocarpine (5) and its regio-isomer "iso-codonocarpine" (22) were effectively separated by droplet counter-current chromatography (DCCC). Codonocarpine and "iso-codonocarpine" were obtained as yellowish prisms of mp 183-187°and of mp 243-246°(decomp.), respectively. Although the direct comparison of our synthetic codonocarpine with an authentic sample was not possible because of no availability of the latter, the comparison of their melting points and their spectral data gave evidence for their identity. Furthermore, N,O-diacetate (23) was confirmed to be completely identical with the authentic sample supplied kindly by Prof. Doskotch. The second topic is concerned with an approach to the total synthesis of two 20-membered ring spermidine dilactam alkaloids, dl-lunarine (6) and dl-lunaridine (7), which have been isolated from the seeds of Lunaria biennis by Boit. After a model experiment (the synthesis of their racemic tetrahydro-derivatives), the synthesis of the racemates of the natural alkaloids was attempted. The key intermediate synthesized by Potier et al. was converted into diamide (40), which was treated with spermidine (4). The separation and characterization of the reaction products are in progress.
- 天然有機化合物討論会の論文
- 1980-09-10
著者
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藤田 栄一
Osaka University Of Pharmaceutical Sciences
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長尾 善光
京大・化研
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瀬野 薫
京大・化研
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宮坂 忠与
京大・化研
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高尾 佐知子
京大・化研
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藤田 栄一
京大・化研
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宮坂 忠与
福山大学薬学部
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長尾 善光
Institute For Chemical Research Kyoto University
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高尾 佐知子
Institute For Chemical Research Kyoto University
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瀬野 薫
Institute For Chemical Research Kyoto University
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