Transformation of D:A-friedo-18.BETA.-lup-19-en-3-one into D:B-friedo-18.BETA.,19.ALPHA.H-lup-5-en-3.BETA.-ol and a comment on the structure of guimarenol.

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概要

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• <I>D</I>:<I>A</I>-friedo-18β-lup-19-en-3-one was transformed into <I>D</I>:<I>B</I>-Friedo-18β,19α<I>H</I>-lup-5-en-3β-ol by two routes, 1) bromination-dehydrobromination of an enol benzoate of <I>D</I>:<I>A</I>-friedo-18β,19α<I>H</I>-lupan-3-one and 2) BF<SUB>3</SUB>·Et<SUB>2</SUB>O-catalyzed backbone rearrangement of 3β,4β-epoxy-<I>D</I>:<I>A</I>-friedo-18β, 19α<I>H</I>-lupane. The 18β<I>H</I>,19α<I>H</I>-configuration in these <I>D</I>:<I>A</I>- and <I>D</I>:<I>B</I>-friedo-type lupane derivatives was determined by means of X-ray diffraction for a 3α,4α-epoxide derived from <I>D</I>:<I>A</I>-friedo-18β,19α<I>H</I>-lupan-3β-ol. The synthetic <I>D</I>:<I>B</I>-friedo-18β,19β<I>H</I>-lup-5-en-3β-ol was found to be not identical with guimarenol isolated from <I>Ceropegia dichotoma</I>.

• 公益社団法人 日本化学会の論文

著者

• Iitaka Yoichi

  Faculty Of Medicine Teikyo University

• Takahashi Takeyoshi

  Department Of Applied Biological Science College Of Agriculture And Veterinary Medicine Nihon Univer

• Tsuyuki Takahiko

  Department Of Chemistry College Of General Education University Of Tokyo

• Yokoyama Yasushi

  Department Of Advanced Materials Chemistry Graduate School Of Engineering Yokohama National Universi

• Moriyama Yoshihiko

  Institute of Chemistry, Kyoto Prefectual University of Medicine

• Itai Akiko

  Faculty of Pharmaceutical Sciences, The University of Tokyo

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