Carbene-catalyzed asymmetric Friedel-Crafts alkylation-annulation sequence and rapid synthesis of indole-fused polycyclic alkaloids

被引：18

作者：

Anwar, Muhammad ^{[1
,2
]}

Yang, Shuang ^{[1
,2
,3
]}

Xu, Weici ^{[1
,2
]}

Liu, Jinggong ^{[4
]}

Perveen, Saima ^{[1
,2
]}

Kong, Xiangwen ^{[1
,2
]}

Zehra, Syeda Tazeen ^{[1
,2
]}

Fang, Xinqiang ^{[1
,2
,3
]}

机构：

[1] Univ Chinese Acad Sci, State Key Lab Struct Chem, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, Fuzhou 350100, Fujian, Peoples R China

[2] Univ Chinese Acad Sci, Key Lab Coal Ethylene Glycol & Its Related Techno, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, Fuzhou 350100, Fujian, Peoples R China

[3] Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

[4] Guangdong Prov Hosp Tradit Chinese Med, Orthoped Dept, Guangzhou 510120, Guangdong, Peoples R China

来源：

COMMUNICATIONS CHEMISTRY | 2019年 / 2卷 / 1期

基金：

中国博士后科学基金;

关键词：

N-HETEROCYCLIC CARBENE; CARBON 4+2 ANNULATION; ENANTIOSELECTIVE SYNTHESIS; DELTA-LACTONES; BETA-LACTONES; HAPALINDOLES;

D O I：

10.1038/s42004-019-0188-2

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Organocatalyzed asymmetric Friedel-Craft reactions have enabled the rapid construction of chiral molecules with highly enantioselectivity enriching the toolbox of chemists for producing complex substances. Here, we report N-heterocyclic carbene-catalyzed asymmetric indole Friedel-Crafts alkylation-annulation with alpha,beta-unsaturated acyl azolium as the key intermediate, affording a large variety of indole-fused polycyclic alkaloids with excellent diastereo- and enantioselectivities. The reaction mechanism is also investigated, and the reaction products can be easily converted to highly functionalized indole frameworks with different core structures.

引用

页数：9

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