Utilization of Protopine and Related Alkaloids. XIII. Attempts to obtain Useful Intermediates for the Syntheses of Chelidonine and Homochelidonine
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概要
- 論文の詳細を見る
The epoxyimine (11a), derived from berberinium chloride, smoothly gives the naphthoquinone epoxide (25a) via several steps. The site-selective reduction of 25a with lithium tri-tert-butoxyaluminohydride affords the cis-epoxy ketol (27a) (45%) and trans isomer (28a) (38%) which result from the attack of the reducing agent at the 4-position. Further reductions of 27a and 28a with sodium borohydride provide the cis-dihydroxy epoxide (32a) and trans isomer (29a), respectively, as a sole product in each case. The desired compounds having the 1-hydroxyl groups trans with respect to the oxirane rings are not formed. Treatment of 32a with methylamine results in the formation of the amide (33a), which is transformed to the isoindolinone (34) and phthalide (35) during purification by preparative thin-layer chromatography using silica gel. The epoxyimine (11b), derived from protopine, gives similar results. The correlation between the proton magnetic resonance data and the structures of the compounds obtained is briefly discussed.
- 公益社団法人日本薬学会の論文
- 1982-02-25
著者
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恩田 政行
School of Pharmaceutical Sciences, Kitasato University
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山口 裕子
Research Laboratories Yoshitomi Pharmaceutical Industries Ltd.
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恩田 政行
Shenyang Pharmaceutical University
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針谷 義弘
北里大薬
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山口 裕子
School of Pharmaceutical Sciences, Kitasato University
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針谷 義弘
School of Pharmaceutical Sciences, Kitasato University
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