防巳科植物アルカロイド研究(第132報)ハスノハカズラのアルカロイド(補遺1)Epistephanineの還元について

  • 富田 真雄
    Pharmaceutical Institute, Medical Faculty, University of Kyoto
  • 渡辺 恭男
    Pharmaceutical Institute, Medical Faculty, University of Kyoto

書誌事項

タイトル別名
  • Studies on the Alkaloids of Menispermaceous Plants. CXXXII. Alkaloids of Stephania japonica Miers (Suppl.1). Hydrogenation of Epistephanine

この論文をさがす

説明

Epistephanine (I : R=CH_3), an alkaloid of Stephania japonica Miers and its dimethiodide (IV), on hydrogenation, did not yield racemic compounds but optically active ones in either case. Epistephanine (I : R=CH_3), on hydrogenation with zinc and sulfuric acid, afforded only hydroepistephanine-A (II) as the dihydro derivative. Treatment of (II) with methyl iodide gave N-methylhydroepistephanine-A dimethiodide (III), which was shown by direct comparison of their specific rotations and infrared spectra to be identical with O-methyloxyacanthine dimethiodide (III)(asymmetric centers, +, -). Epistephanine dimethiodide (IV), when reduced with either sodium borohydride or zinc-sulfuric acid, afforded N-methylhydroepisephanine monomethiodide, from which N-methylhydroepistephanine-B dimethiodide (VI) was derived. It was found that (VI) is identical with O-methylrepandine dimethiodide (IX)(asymmetric centers, +, +) by infrared spectral determinations, and that since the values of their specific rotations have the opposite sign to each other, (VI) is an antipode of (IX) and hence its asymmetric centers are (-, -).

収録刊行物

詳細情報 詳細情報について

  • CRID
    1571135652444883456
  • NII論文ID
    110003617704
  • NII書誌ID
    AA00348119
  • 本文言語コード
    en
  • データソース種別
    • CiNii Articles

問題の指摘

ページトップへ