Acid-catalyzed backbone rearrangement of 5,6-epoxyalnusanes and preparation of daturadiol.

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概要

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• Epoxidation of alnus-5-en-3β-yl acetate with <I>m</I>-chloroperbenzoic acid gave a 5β,6β-epoxide as a main product together with a 5α,6α-epoxide as a minor product. Treatment of the α-epoxide with BF<SUB>3</SUB>·OEt<SUB>2</SUB> afforded a 1(10),5-diene and a mixture of 6α-hydroxy-12- and -18-ene derivatives. The 12-ene was converted into daturadiol (=olean-12-ene-3β,6β-diol).

• 公益社団法人 日本化学会の論文

著者

• Iitaka Yoichi

  Faculty Of Medicine Teikyo University

• Itai Akiko

  Faculty of Pharmaceutical Sciences, University of Tokyo

• Matsumoto Yuzo

  Department Of Neurological Surgery Okayama University Medical School

• Takai Masaki

  Department Of Biological Function And Genetic Resources Science Faculty Of Agriculture Okayama Unive

• 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

• Iitaka Yoichi

  Faculty of Pharmaceutical Sciences, The University of Tokyo

• Moriyama Yoshihiko

  Institute of Chemistry, Kyoto Prefectual University of Medicine

• Tori Motoo

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Ohnishi Hiraku

  Faculty of Pharmaceutical Sciences, The University of Tokyo

• Itai Akiko

  Faculty of Pharmaceutical Sciences, The University of Tokyo

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