44 フッキソウのフリーデリン型新トリテルペンの構造

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概要

• 論文の詳細を見る

• Pachysandiol-B (IIa) and pachysonol (IIIa) are new triterpenes isolated from Pachysandra terminalis SIEB. et ZUCC. and their interrelationship was indicated by the partial acetylation of IIa followed by CrO_3 oxidation, yielding pachysonol acetate (IIIb). The ORD curve and the bromination experiments of IIIb suggested that the compounds (IIa, IIIa) are the members of friedelin series. This was proved by the reaction of IIIa with mesyl chloride, which gave mainly a rearranged product (tentatively assigned to XI) and a small amount of anhydro compound (XII). The latter, on hydrogenation, afforded a saturated ketone whose IR spectrum (KBr) was almost superimposable upon that of friedelin. Additional evidence was provided by the acid induced rearrangement of an unsaturated ketone (X) derived from IIa (IIa→VI→VIIIa→X). The major product was found to be XIV on the basis of chemical and spectral evidences. Therefore the structure of pachysandiol-B and pachysonol are assigned to IIa and IIIa, respectively. The configuration of the 16-hydroxyl group is now under investigation. The triol (XVIa) is a minor triterpene which was characterized as its triacetate (XVIb) and diacetate (XVIc). The CrO_3 oxidation of XVIc gave a keto-diacetate (XVII), which on alkali treatment afforded a diosphenol (XVIII) and on alumina chromatography isomerized easily to give XIX. The Wolff-Kishner reduction of both XVII and XIX followed by acetylation gave rise to a saturated acetate (IXb) which was identified with IXb obtained from IIIb. Thus the structure of the triol is assigned to XVIa.

• 天然有機化合物討論会の論文
• 1970-10-01

著者

• 有本 昌弘

  Faculty Of Pharmaceutical Sciences Kyoto University

• 菊池 徹

  Faculty Of Pharmaceutical Sciences Kyoto University

• 菊池 徹

  京大薬学部

• 菊池 徹

  京大薬学科

• 高山 雅治

  京大薬

• 小山 峰雄

  京大薬

• 有本 昌弘

  京大薬

関連論文

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• Structure of Sargatriol, a New Isoprenoid Chromenol from a Marine Alga : Sargassum tortile
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• Application of Homonuclear INDOR Spectroscopy in Friedelin Type Triterpenes
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• 40 フッキソウアルカロイドの相互変換 : Pachystermine-A及び-Bの合成
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• 44 フッキソウのフリーデリン型新トリテルペンの構造
• フッキソウの中性成分(第2報) : Taraxerolの確認およびCompound-IIIA, IIIBの分離
• フッキソウの中性成分(第1報) : SterolおよびTriterpeneの分離
• 白頭翁の成分研究

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