A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light

被引：21

作者：

Gao, Yu-Qi ^{[1
]}

Hou, Yi ^{[1
]}

Zhu, Liming ^{[2
]}

Chen, Guzhou ^{[1
]}

Xu, Dongyang ^{[1
]}

Zhang, Sheng-Yong ^{[3
]}

He, Yupeng ^{[2
]}

Xie, Weiqing ^{[1
,4
]}

机构：

[1] Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, 22 Xinong Rd, Yangling 712100, Shaanxi, Peoples R China

[2] Liaoning Shihua Univ, Coll Chem Chem Engn & Environm Engn, Dandong Lu West 1, Fushun 113001, Peoples R China

[3] Fourth Mil Med Univ, Dept Chem, Xian 710032, Shaanxi, Peoples R China

[4] Key Lab Bot Pesticide R&D Shaanxi Prov, Yangling 712100, Shaanxi, Peoples R China

来源：

RSC ADVANCES | 2019年 / 9卷 / 50期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; ACID; ANTHOCYANIDINS; PHLOROGLUCINOL; BIOSYNTHESIS; CONSTRUCTION; YUREMAMINE; CATALYSIS; SALTS;

D O I：

10.1039/c9ra07198a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A bio-inspired synthesis of hybrid flavonoids from 2-hydroxylchalcone is described. Under the irradiation of 24 W CFL, 2-hydroxychalcone reacts with various nucleophiles to deliver structurally diverse hybrid flavonoids in good to excellent yields in the presence of a catalytic Bronsted acid. Moreover, moderate enantioselectivities could be obtained using a catalytic chiral phosphoric acid via counter anion directed addition. Based on mechanistic studies, the reaction is proposed to proceed via tandem double-bond isomerization/dehydrated cyclization of 2-hydroxychalcone to form a transient flavylium cation, which is in situ captured by nucleophiles to afford hybrid flavonoids.

引用

页码：29005 / 29009

页数：5

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