2-Nitropyrrole cross-coupling enables a second generation synthesis of the heronapyrrole antibiotic natural product family

被引：10

作者：

Ding, Xiao-Bo ^{[1
]}

Furkert, Daniel P. ^{[1
]}

Brimble, Margaret A. ^{[1
,2
]}

机构：

[1] Univ Auckland, Sch Chem Sci, 23 Symonds St, Auckland 1010, New Zealand

[2] Univ Auckland, Maurice Wilkins Ctr Mol Biodiscovery, Private Bag 92019, Auckland 1010, New Zealand

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 85期

关键词：

HUNSDIECKER REACTION; DECARBOXYLATIVE BROMINATION; CARBOXYLIC-ACIDS; SULFONIUM SALTS; EFFICIENT; BIOSYNTHESIS; CATALYST;

D O I：

10.1039/c6cc07532k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The heronapyrroles are a family of antibiotic natural products containing the rare 2-nitropyrrole motif. We report here a second generation total synthesis that circumvents problems of selective pyrrole nitration and alkene formation that limited the utility of previous approaches. Stille sp(3)-sp(2) cross coupling of a novel 2-nitropyrrole fragment was developed to install the key C7,8 olefin with complete regiochemical control. An unusual Hunsdiecker-type decarboxylative halogenation was also identified, providing access to the complex vinyl stannane coupling partners required for formation of the natural product.

引用

页码：12638 / 12641

页数：4

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