Total Synthesis of Chaetominine

被引:73
作者
Toumi, Mathieu [1 ]
Couty, Frangois [1 ]
Marrot, Jerome [1 ]
Evano, Gwilherm [1 ]
机构
[1] Univ Versailles, UMR CNRS 8180, Inst Lavoisier Versailles, F-78035 Versailles, France
关键词
D O I
10.1021/ol802155n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, asymmetric synthesis of the cytotoxic natural product chaetominine was achieved in 14 steps. The strategy employs a copper(l)mediated cyclization reaction as a key step to install the abc-tricyclic ring system, which was further elaborated by diastereoselective oxidation and reduction reactions. This effort also documents the first example of an oxidative rearrangement yielding to homochiral spirocyclic pyrrolidinyloxindoles.
引用
收藏
页码:5027 / 5030
页数:4
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