O-Methylation Effect on the Carbon-13 Nuclear Magnetic Resonance Signals of ortho-Disubstituted Phenols and Its Application to Structure Determination of New Phthalides from Aspergillus silvaticus
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概要
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The O-methylation effect on the carbon-13 nuclear magnetic resonance chemical shifts of ortho-disubstituted phenols was investigated. In phenols with nonconjugated ortho-disubstituents (1-10), O-methylation caused a downfield shift by an average of 5.2 ppm for the ortho-carbons (C-2 and -6), and a downfield shift by an average of 4.6 ppm for the para-carbon (C-4). These shift values are significantly different from those observed in ortho-monosubstituted and ortho-nonsubstituted phenols. This regularity is very useful for the spectral interpretation of some natural products with an ortho-disubstituted phenol group and for the determination of the position of the methoxy group in such compounds. Two new phthalides, silvaticol (15) and O-methylsilvaticol (16), were isolated along with nidulol (17) from Aspergillus silvaticus. In the course of the structure determination of these compounds, the O-methylation effects of ortho-mono-and ortho-disubstituted phenols were successfully applied to these phthalides. The structures of silvaticol and O-methylsilvaticol were determined as 6-hydroxy-4-methoxy-5-methylphthalide and 4,6-dimethoxy-5-methylphthalide, respectively.
- 1984-07-25
著者
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河合 賢一
星薬大
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河合 賢一
Faculty of Pharmaceutical Sciences, University of Tokyo
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河合 賢一
Faculty Of Pharmaceutical Sciences Hoshi University
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中島 正一
星薬科大学
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永井 正博
Institute of Medicinal Chemistry Hoshi University
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藤田 正雄
Faculty of Pharmaceutical Sciences Hoshi University
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永井 正博
星薬科大学生薬学教室
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山田 美紀子
Faculty Of Pharmaceutical Sciences Chiba University
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藤田 正雄
Faculty Of Pharmaceutical Sciences:hoshi University
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中嶋 正一
Faculty of Pharmaceutical Sciences Hoshi University
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藤田 正雄
星薬科大学薬学部:(現)株式会社ウチダ和漢薬研究開発室
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