Intramolecular Direct Dehydrohalide Coupling Promoted by KOtBu: Total Synthesis of Amaryllidaceae Alkaloids Anhydrolycorinone and Oxoassoanine

被引：123

作者：

De, Subhadip ^{[1
]}

Ghosh, Santanu ^{[1
]}

Bhunia, Subhajit ^{[1
]}

Sheikh, Javeed Ahmad ^{[1
]}

Bisai, Alakesh ^{[1
]}

机构：

[1] IISER, Dept Chem, Bhopal 462023, MP, India

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 17期

关键词：

CATALYZED DIRECT ARYLATION; C-H ACTIVATION; CHEMICAL-CONSTITUENTS; HIPPADINE; BUTOXIDE; ACIDS; FUNCTIONALIZATION; (HETERO)ARENES; SUBSTITUTION; HETEROCYCLES;

D O I：

10.1021/ol3019677

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution (HAS) with aryl radicals has been developed in the presence of potassium tert-butoxide and an organic molecule as the catalyst. The methodology has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), and other related structures. Interestingly, the method also works only in the presence of potassium tert-butoxide.

引用

页码：4466 / 4469

页数：4

共 55 条

[1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].