Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction.
Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction.
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通过 Staudinger/aza-Wittig 反应形成奥佩酰胺的 BC 环系统。
DOI：
10.1021/ol702255k
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发表时间：
2007
期刊：
影响因子：
5.2
通讯作者：
Sulikowski,GaryA
中科院分区：
文献类型：
--
作者：
Luo,Zhushou;Peplowski,Katherine;Sulikowski,GaryA
通过立体选择性的Diels-−-Alder反应和Staudinger/aza-Wittig/亚胺的水解反应组装了苯甲酰胺的BC环体系。立体选择性的羟醛与结合了DE环体系的醛的偶联导致了一种先进的合成中间体，该中间体在合成海洋生物碱丁苯酰胺的过程中被发现。
The BC ring system of upenamide was assembled using a stereoselective Diels−Alder reaction followed by a Staudinger/aza-Wittig/imine hydrolysis reaction. Stereoselective aldol coupling with an aldehyde that incorporates the DE ring system led to an advanced synthetic intermediate en route to the marine alkaloid upenamide.