Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products

被引：56

作者：

Bao, Kai ^{[1
,2
]}

Fan, Aixue ^{[1
]}

Dai, Yi ^{[2
]}

Zhang, Liang ^{[1
]}

Zhang, Weige ^{[1
]}

Cheng, Maosheng ^{[1
]}

Yao, Xinsheng ^{[2
]}

机构：

[1] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang, Peoples R China

[2] Jinan Univ, Inst Tradit Chinese Med & Nat Prod, Guangzhou, Guangdong, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 24期

基金：

美国国家科学基金会;

关键词：

DEALKYLATION; DERIVATIVES;

D O I：

10.1039/b916969e

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

An efficient selective demethylation and debenzylation method for aryl methyl/benzyl ethers using magnesium iodide under solvent-free conditions has been developed and applied to the synthesis of natural flavone and biphenyl glycosides. A variety of functional groups including glycoside were tolerated under the reaction conditions. Experimental results indicated that the removal of an O-benzyl group was easier than that of an O-methyl group, regardless of wherever they were meta or para to the carbonyl. Thus selective debenzylation can be achieved for substrates bearing both benzyloxy and methoxy groups.

引用

页码：5084 / 5090

页数：7

共 22 条

[1]

An efficient synthesis of the phytoestrogen 8-prenylnaringenin from isoxanthohumol with magnesium iodide etherate [J].