Heterocycles. XI. Syntheses of Analogs of 10b-Hydroxychelidonine and 4b-Epichelidonine
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概要
- 論文の詳細を見る
The naphthoquinone epoxide (4), derived from the naphthoquinone (1), is reduced with sodium borohydride under mild conditions to yield the cis-epoxy ketol (5) exclusively. The configuration of the 4-hydroxyl group in 5 is deduced on the basis of the intramolecular hydrogen-bonding observed in the infrared spectrum. Further reduction of 5 with sodium borohydride gives the cis-epoxyhydroxy lactone (7) as a main product, which is stereoselectively converted into the 10b-hydroxychelidonine (17) and 4b-epichelidonine analogs (19) by the following procedures : aminolysis with methylamine (7→13), reduction with lithium aluminum hydride (13→14), hydrogenolysis over a palladium catalyst (14→17), dehydration with mesyl chloride (17→18) and reduction with lithium aluminum hydride/aluminum chloride (18→19). The stereostructures for these compounds are deduced from the infrared and proton magnetic resonance data.
- 公益社団法人日本薬学会の論文
- 1981-09-25
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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高松 生子
School of Pharmaceutical Sciences, Kitasato University
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四元 孝子
School of Pharmaceutical Sciences, Kitasato University
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高松 生子
School Of Pharmaceutical Sciences Kitasato University
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四元 孝子
School Of Pharmaceutical Sciences Kitasato University
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