Total synthesis of two isoflavone C-glycosides:: genistein and orobol 8-C-β-D-glucopyrano sides

被引：38

作者：

Sato, Shingo ^{[1
]}

Hiroe, Kaoru ^{[1
]}

Kumazawa, Toshihiro ^{[1
]}

Jun-Ichi, Onodera ^{[1
]}

机构：

[1] Yamagata Univ, Fac Engn, Dept Chem & Chem Engn, Yonezawa, Yamagata 9928510, Japan

来源：

CARBOHYDRATE RESEARCH | 2006年 / 341卷 / 09期

关键词：

isoflavone C-glycosides; total synthesis; C-glycosylation; oxidative rearrangement; O-debenzylation;

D O I：

10.1016/j.carres.2006.03.038

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Genistein and orobol 8-C-beta-D-glucopyranosides (1 and 3) were firstly synthesized in overall yields of 39% and 41% from 2,4-di-O-benzylphloroacetophenone (4), as follows: (1) the formation of the chalcone (6, 7) by aldol condensation of the benzyl-protected C-glycosylphloroacetophenone (5), a key intermediate of the total synthesis of I and 3 and synthesized by a C-glycosylation method involving the O -> C glycoside rearrangement of 4 in 96% yield; (2) the formation of isoflavones (10, 11 and 12, 13) by the formation of acetals by oxidative rearrangement of the protected chalcones (8 and 9) using TI(NO3)(3), followed by acid-catalyzed cyclization: (3) a final debenzylation by hydrogenolysis. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1091 / 1095

页数：5

共 46 条

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