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
收藏
页码：12638 / 12641
页数：4
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