Double conjugate addition of a nitropropionate ester to a quinone monoketal:: Synthesis of an advanced intermediate to (±)-gelsemine
Double conjugate addition of a nitropropionate ester to a quinone monoketal:: Synthesis of an advanced intermediate to (±)-gelsemine
复制标题
DOI：
10.1021/ol071174p
复制
发表时间：
2007-08-02
期刊：
影响因子：
5.2
通讯作者：
Aube, Jeffrey
中科院分区：
文献类型：
--
作者：
Grecian, Scott;Aube, Jeffrey
[图表] 3-硝基丙酸乙酯的双阴离子锂和对苯醌二甲基缩酮之间的双共轭加成得到非对映体[3.2.1]二环辛酮的混合物。这些产品被转化为一种高级中间体，之前由 Fukuyama 和 Liu 转化为 (+/-)-gelsemine。
[GRAPHICS]A double conjugate addition between the lithium dianion of ethyl 3-nitropropionate and p-benzoquinone dimethyl ketal afforded a mixture of diastereomeric [3.2.1]bicylooctanones. These products were converted into an advanced intermediate previously carried forward to (+/-)-gelsemine by Fukuyama and Liu.