Hypervalent Iodine(III)-Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C

被引：20

作者：

Tian, Guilong ^{[1
]}

Fedoseev, Pavel ^{[1
]}

van der Eycken, Erik V. ^{[1
,2
]}

机构：

[1] Univ Leuven, KU Leuven, LOMAC, Celestijnenlaan 200F, B-3001 Leuven, Belgium

[2] Peoples Friendship Univ Russia, RUDN Univ, 6 Miklukho Maklaya St, Moscow 117198, Russia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 22期

关键词：

2-aminoimidazoles; cascade reactions; guanidines; hypervalent iodine; kealiinine alkaloids; PSEUDOMONAS-AERUGINOSA; BIOFILM FORMATION; INHIBITORS; ANALOGS; CERATAMINE; ALKALOIDS; BINDING;

D O I：

10.1002/chem.201700934

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An oxidative cascade cyclization of propargylguanidines promoted by phenyliodonium diacetate (PIDA) was developed. The protocol provides an efficient route for the synthesis of the alkaloids kealiinines B and C as well as homologues. The difference in the electronic nature of the acetylene substituent resulted in two ways of the cyclization. A plausible mechanism is proposed based on the experimental results.

引用

页码：5224 / 5227

页数：4

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