Total synthesis of (+)-frondosin A. Application of the Ru-catalyzed [5+2] cycloaddition

被引：94
|
作者：
Trost, Barry M. [1 ]
Hu, Yimin [1 ]
Horne, Daniel B. [1 ]
机构：
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 38期
关键词：
D O I：
10.1021/ja073272b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first total synthesis of (+)-frondosin A was accomplished in 19 longest linear and 21 total steps from commercially available materials. The key features of the synthesis include a Ru-catalyzed [5+2] cycloaddition, a Claisen rearrangement, and a ring expansion to construct the core of the frondosin A in a diastereoselective and regioselective fashion. This is the first application of a Ru-catalyzed [5+2] cycloaddition in the total synthesis of a natural product. Through this synthesis, the absolute configuration of (+)-frondosin A was established.
引用
收藏
页码：11781 / 11790
页数：10
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