A new route to platencin via decarboxylative radical cyclization

被引：12
|
作者：
Moustafa, Gamal A. I. [1 ]
Saku, Yuki [1 ]
Aoyama, Hiroshi [1 ]
Yoshimitsu, Takehiko [1 ]
机构：
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
来源：
CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 99期
关键词：
FORMAL TOTAL-SYNTHESIS; CARBOXYLIC-ACIDS; PLATENSIMYCIN; (+/-)-PLATENCIN; ALKENYLATION; INHIBITOR; DISCOVERY; OXIDATION; FABF;
D O I：
10.1039/c4cc07316a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new approach to platencin, a potent antibiotic isolated from Streptomyces platensis, has been established. The highly congested tricyclic core of the natural product was successfully constructed by decarboxylative radical cyclization of an alkynyl silyl ester with Pb(OAc)(4) in the presence of pyridine in refluxing 1,4-dioxane. The key decarboxylation, which likely takes place via lead(IV) esterification followed by carbon-centered radical generation and subsequent capture of the radical with a triple bond, allows the rapid construction of the twisted polycyclic system.
引用
收藏
页码：15706 / 15709
页数：4
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