Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (±)-aspidophytine

被引:124
作者
Mejia-Oneto, Jose M. [1 ]
Padwa, Albert [1 ]
机构
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
关键词
D O I
10.1021/ol061137i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy for the synthesis of (+/-)-aspidophytine has been developed and is based on a Rh(II)-catalyzed cyclization/dipolar cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provides the complete skeleton of aspidophytine. The synthesis also features a mild decarbomethoxylation reaction.
引用
收藏
页码:3275 / 3278
页数:4
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