24 (±)Hasubanonineの合成
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概要
- 論文の詳細を見る
The total synthesis of (±)-hasubanonine (56) has now been accomplished as follows. The compound (36), the synthesis of which had been reported in a previous paper, was chosen as a starting material in a present synthesis. Ketalization, demethylation, acetylation, and deketalization of the compound (36) gave the compound (44). Oxidation of (44) with Pb(OAc)_4, followed by bromination with pyridine-hydrobromide perbromide afforded the compound (46). Rearrangement reaction of the compound (46) with NaOAc-AcOH gave the compound (47), the partial hydrolysis of which afforded the compound (48). Bromination of (48), followed by methylation gave the compound (50). Treatment of (50) with 5% H_2SO_4-H_2O-dimethoxyethane in a sealed tube at 150-155° for 24hr afforded the compound (51) in a 30% yield. Methylation of (51) with diazomethane afforded the compound (52) together with its structural isomer (53). Separation of the compound (52) and (53) was effected by fractional crystallization. The desired product (52) was proved to be identical with 16-oxo-hasubanonine (35) which was transformed from natural hasubanonine by oxidation with KMnO_4. On the other hand, LiAlH_4 reduction of 16-oxo-hasubanonine, followed by MnO_2 oxidation regenerated hasubanonine.
- 天然有機化合物討論会の論文
- 1970-10-01
著者
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田中 圭
Faculty Of Pharmaceutical Sciences Kyoto University
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田中 圭
静岡県大 薬
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井深 俊郎
Faculty Of Pharmaceutical Sciences Kyoto University
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犬伏 康夫
京大薬学科
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犬伏 康夫
Faculty Of Pharmaceutical Sciences Kyoto University
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井深 俊郎
京大薬
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田中 圭
京大薬
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田中 圭
京都大学薬学部
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