The Efficient Synthesis of Benzannulated Seven-Membered O-Heterocycles via the Intramolecular Ring-Opening Cyclization of Cyclopropanes

被引：25

作者：

Cao, Dongpo ^{[1
]}

Zhang, Kaipeng ^{[1
]}

An, Ran ^{[1
]}

Xu, Hang ^{[1
]}

Hao, Shuang ^{[1
]}

Yang, Xiaoguang ^{[1
]}

Hou, Zhuang ^{[1
]}

Guo, Chun ^{[1
]}

机构：

[1] Shenyang Pharmaceut Univ, Key Lab Struct Based Drugs Design & Discovery, Minist Educ, Sch Pharmaceut Engn, Shenyang 110016, Liaoning, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 22期

基金：

中国国家自然科学基金;

关键词：

FUNGUS;

D O I：

10.1021/acs.orglett.9b03260

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical approach for the synthesis of substituted benzannulated seven-membered O-heterocycles from cyclopropane derivatives is described. The transformation proceeds via Lewis acid mediated ring opening of cyclopropanes followed by a concomitant 7-endo-tet cyclization to furnish the 4-benzoyl-3,4-dihydrobenzo[b]oxepin-5(2H)-one derivatives in excellent yields (up to 92%). This potentially general method is featured by its high atom economy, broad substrate scope, and mild reaction conditions. Moreover, the representative products exhibited selective antifungal activity in vitro against the fungus Cryptococcus neoformans. Therefore, the present reaction will be useful for the development of novel antifungal therapeutic reagents.

引用

页码：8948 / 8951

页数：4

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