Bromoetherification-based strategy towards the spirocyclic chromophore of chlorofusin

被引：15

作者：

Wei, Wan-Guo ^{[1
]}

Qian, Nven-Jian ^{[1
]}

Zhang, Yong-Xia ^{[1
]}

Yao, Zhu-Jun ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 25期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetlet.2006.04.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and direct route to the racemic model chromophore of the potent p53-MDM2 antagonist, chlorofusin, is presented. The spirocyclic chromophores were successfully constructed in high yields by an NBS-mediated intramolecular haloetherification. Ring expansion was observed in the subsequent reaction of the bromides with silver nitrate in refluxing acetone and water. Conversion of the bromides to the desired ketones was finally achieved by NMO oxidation. All four possible isomeric chromophores were finally synthesized and unambiguously characterized by X-ray crystallography studies. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4171 / 4174

页数：4

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