Regio- and Stereoselective Electrophilic Cyclization Approach for the Protecting-Group-Free Synthesis of Alkaloids Lennoxamine, Chilenine, Fumaridine, 8-Oxypseudoplamatine, and 2-O-(Methyloxy)fagaronine

被引：21

作者：

Yao, Tuanli ^{[1
,2
]}

Guo, Zhen ^{[1
]}

Liang, Xiujuan ^{[1
]}

Qi, Lihan ^{[1
]}

机构：

[1] Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Xian 710021, Shaanxi, Peoples R China

[2] Shaanxi Univ Sci & Technol, Shaaxi Key Lab Chem Addit Ind, Xian 710021, Shaanxi, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 21期

关键词：

A-C; ISOINDOLOBENZAZEPINE; DERIVATIVES; INHIBITORS; CASCADE; HETEROCYCLES;

D O I：

10.1021/acs.joc.8b02154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A unified strategy for protecting-group-free synthesis of alkaloids lennoxamine, chilenine, fumaridine, 8-oxypseudoplamatine, and 2-O-(methyloxy)fagaronine is reported. The core isoindolin-1-one and isoquinolin-1-one structures were built by a silver-catalyzed regio- and stereoselective cyclization of methyl 2-alkynylbenzimidates. The regioselectivity of cyclization was achieved by utilizing the intrinsic functionality of alkaloids.

引用

页码：13370 / 13380

页数：11