Transformation of 2,3-Dibenzylbutyrolactone Lignans containing a Secondary Hydroxyl Group to Phenyltetralin Lignans and Their Reduction Products with Lithium Aluminum Hydride

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概要

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• Two 2,3-dibenzylbutyrolactone lignans containing a secondary hydroxyl group at one of the benzylic positions, 5-hydroxyarctigenin (I) and 5-hydroxytrachelogenin (XI), were transformed to phenyltetralin lignans, α-conidendrin monomethyl ether (II) and 3-hydroxy-α-conidendrin monomethyl ether (XII), respectively, by acid treatment. The hemiacetal lignan, (1S, 2R, 3S, 3aR) 6,7-dimethoxy-3-hydroxy-2-hydroxymethyl-1-3', 4'-dimethoxyphenyl-1,2,3,4-tetrahydronaphthalene-3-carboxylic acid lactol (XV), was obtained in addition to isoolivil dimethyl ether (XIV), the normal reduction product, when 3-hydroxy-α-conidendrin dimethyl ether (XIII) was treated with lithium aluminum hydride, and a mechanism is proposed for this reaction.

• 公益社団法人日本薬学会の論文
• 1981-07-25

著者

• 西部 三省

  Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido

• 滝戸 道夫

  Department of Pharmacy, College of Science and Technology, Nihon University

• 山内 盛

  College of Science and Technology, Nihon University

• 久田 末雄

  Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University

• 久田 末雄

  Faculty Of Pharmaceutical Sciences Higashi Nippon Gakuen University

• 滝戸 道夫

  日本大学薬学部生薬学研究室

• 塚本 博樹

  Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University

• 山内 盛

  Department of Pharmacy, College of Sciences and Technology, Nihon University

• 西部 三省

  北海道医療大 薬

• 塚本 博樹

  Faculty Of Pharmaceutical Sciences Higashi Nippon Gakuen University

• 西部 三省

  Faculty Of Pharmaceutical Sciences Health Sciences University Of Hokkaido

• 山内 盛

  College Of Science And Technology Nihon University

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