Asymmetric Organocatalytic Synthesis of Benzopyran- and Benzofuran-Fused Polycyclic Acetals

被引：30
作者：
Yang, Jiyang [1 ,2 ]
Qiu, Gang [1 ,2 ,4 ]
Jiang, Jing [1 ,2 ]
Hu, Yanwei [1 ,2 ]
Chen, Shaohua [1 ,2 ]
Zhang, Shilei [1 ,2 ]
Zhang, Yinan [1 ,2 ,3 ]
机构：
[1] Soochow Univ, Coll Pharmaceut Sci, Jiangsu Key Lab Translat Res & Therapy Neuropsych, Suzhou 215123, Peoples R China
[2] Soochow Univ, Coll Pharmaceut Sci, Dept Med Chem, Suzhou 215123, Peoples R China
[3] Univ Kentucky, Coll Pharm, 789 South Limestone St, Lexington, KY 40536 USA
[4] Haiyan Peoples Hosp, 901 South Yanhu Rd,Wuyuan St, Haiyan, Zhejiang 314300, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 13期
基金：
中国国家自然科学基金;
关键词：
benzofurans; benzopyrans; enantioselectivity; heterocycles; organocatalysis; ENANTIOSELECTIVE MICHAEL ADDITION; ALDER-TYPE ADDUCTS; DOMINO REACTIONS; EFFICIENT SYNTHESIS; CONJUGATE ADDITION; CYCLIC HEMIACETALS; NATURAL-PRODUCTS; SILYL ETHERS; C-F; ALDEHYDES;
D O I：
10.1002/adsc.201601335
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient organocatalytic method for the asymmetric preparation of benzopyran-and benzofuran-fused polycyclic acetals is described for the first time. This useful approach includes an interesting tunable Michael-acetalization of nitrostyrenes or a-aromatization-acetalization of quinones. Under mild conditions, simple cyclic hemiacetals could be stereoselectively converted into four different types of polyheterocycles that serve as scaffolds for a number of bioactive natural products.
引用
收藏
页码：2184 / 2190
页数：7
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