Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XXIV. A Convenient Method for Synthesizing 6- and 8-Methoxylated 5,7-Dihydroxyisoflavones

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概要

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• 2', 4'-Bis(benzyloxy)-3', 6'-dimethoxychalcones (5), which were obtained from the dibenzyl ether of 2,4-dihydroxy-3,6-dimethoxyacetophenone (3), were oxidatively rearranged with thallium (III) nitrate in methanol and the resultant products were converted into 7-hydroxy-5,8-dimethoxyisoflavones (8) by hydrogenolysis, followed by cyclization. The isoflavones were quantitatively demethylated to 5,7-dihydroxy-8-methoxyisoflavones (2) via their acetates. The isomeric 5,7-dihydroxy-6-methoxyisoflavones (1) were also synthesized from the chalcones, obtained from 2,3-dimethoxy- (16) or 2-isopropoxy-3-methoxy-4,6-bis(benzyloxy)acetophenones (21), by a similar method. On the other hand, the isoflavones with two hydroxy groups at the 2'- and 4'-positions were easily synthesized by the following method. Treatment of the rearranged product from 2,2', 4,4'-tetrakis(bezyloxy)-3', 6'-dimethoxychalcone (5f) with hydrochloric acid (HCl) in acetic acid afforded 2', 4', 7-tris(benzyloxy)-5,8-dimethoxyisoflavone (10f). The 5-methoxy group in the isoflavone was quantitatively cleaved to give the corresponding 5-hydroxyisoflavone (11f), which was isomerized to 2', 4', 7-tris(benzyloxy)-5-hydroxy-6-methoxyisoflavone (25f) in the presence of anhydrous potassium carbonate. Hydrogenolysis of the two 5-hydroxyisoflavones proceeded smoothly to give 2', 4', 5,7-tetrahydroxy-8-(2f) and 6-methoxyisoflavones(1f), respectively. The ^<13>C-NMR spectra of these isoflavones supported the proposed structures of polyhydroxyisoflavones. The proposed structures of two natural isoflavones were revised.

• 公益社団法人日本薬学会の論文
• 1998-02-15

著者

• Sugimoto K

  Department Of Hygiene Hamamatsu University School Of Medicine

• Fujii Kenichi

  Department of Internal Medicine, Division of Coronary Heart Disease

• 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

• Fujii Kenichi

  Department Of Cardiology Himeji Cardiovascular Center

• TSUKAYAMA Masao

  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

  Midori Kagaku Co., Ltd.,

• OHTSURU Yoshizumi

  Midori Kagaku Co., Ltd.,

• Horie T

  Midori Kagaku Co. Ltd.

• Tsukayama M

  Univ. Tokushima Tokushima Jpn

• Ohtsuru Yoshizumi

  Midori Kagaku Co. Ltd.

• Fujii Kenichi

  Department Of Applied Physics Faculty Of Engineering Osaka University

• Fujii Kenichi

  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

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