Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XXII. A Convenient Method for Synthesizing 3,5,7-Trihydroxy-6-methoxyflavones

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概要

• 論文の詳細を見る

• The demethylation of 3,4-dioxygenated 6-methoxy-2-isopropoxyacetophenones was studied and it was found that 4-benzyloxy-6-hydroxy-3-methoxy-2-isopropoxyacetophenone was easily obtained from 4-benzyloxy-3,6-dimethoxy-2-isopropoxyacetophenone by selective demethylation with anhydrous aluminum bromide-sodium iodide in acetonitrile. The acetophenone was converted into 7-benzyloxy-3-hydroxy-6-methoxy-5-isopropoxyflavones by cyclization followed by oxidation with dimethyldioxirane. The isopropoxy group in the flavones was selectively cleaved with anhydrous aluminum chloride via the corresponding tosylates to give 7-benzyloxy-3,5-dihydroxy-6-methoxyflavones, which were converted into the desired 3,5,7-trihydroxy-6-methoxyflavones by hydrogenolysis. The process was suitable as a general method for synthesizing 3,5,7-trihydroxy-6-methoxyflavones and five flavones were synthesized. We also examined the ^<13>C-NMR spectra of twelve kinds of 3,5,6,7-tetraoxygenated 4'-methoxyflavones and revised the proposed structure of a natural flavone.

• 公益社団法人日本薬学会の論文
• 1997-03-15

著者

• Sugimoto K

  Department Of Hygiene Hamamatsu University School Of Medicine

• Shibata Kiyoshi

  Equipment Center

• Shibata Kenichi

  Department Of Chemical Science And Technology Faculty Of Engineering The University Of Tokushima

• Yamashita Kazumi

  Faculty Of Pharmaceutical Sciences Okayama University

• TSUKAYAMA Masao

  Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima

• KAWAMURA Yasuhiko

  Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima

• YAMASHITA Kazuyo

  Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima

• Tsukayama M

  Department Of Chemical Science And Technology Faculty Of Engineering The University Of Tokushima

• Tsukayama Masao

  Department Of Chemical Science And Technology Fachnology Faculty Of Engineering The University Of To

• Yamashita K

  Department Of Chemical Science And Technology Faculty Of Engineering The University Of Tokushima

• Horie Tokunaru

  Department of Applied Chemistry, Faculty of Engineering, Tokushima University

• HORIE Tokunaru

  Midori Kagaku Co., Ltd.,

• Horie T

  Midori Kagaku Co. Ltd.

• Tsukayama M

  Univ. Tokushima Tokushima Jpn

• Kawamura Y

  Department Of Chemical Science And Technology Faculty Of Engineering The University Of Tokushima

• Kawamura Yasuhiko

  Department Of Chemical Science And Technology Faculty Of Engineering The University Of Tokushima

• Tsukayama Masao

  Department Of Biological Science And Technology The University Of Tokushima Graduate School

• Kawamura Yasuhiko

  Department of Applied Chemistry, Faculty of Engineering, Tokushima University

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