The total synthesis of (+)-hapalindole Q by an organomediated Diels-Alder reaction
The total synthesis of (+)-hapalindole Q by an organomediated Diels-Alder reaction
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DOI：
10.1021/ja036191y
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发表时间：
2003-11-19
影响因子：
15
通讯作者：
Kerr, MA
中科院分区：
文献类型：
--
作者：
Kinsman, AC;Kerr, MA
实现了(+)-哈帕吲哚Q的全合成。关键步骤是由MacMillan的有机催化剂催化的Diels-Alder反应，以提供具有高对映选择性(93%ee)的关键中间体。这一步骤建立了所需的四个连续立体中心的正确排列，包括四个四元中心，并首次成功地将不对称有机甲基化Diels-Alder反应应用于全合成。
The total synthesis of (+)-hapalindole Q has been achieved. The key step is a Diels-Alder reaction mediated by MacMillan's organocatalyst to provide the critical intermediate with high enantioselectivity (93% ee). This step establishes the proper arrangement of the required four contiguous stereocenters, including the quaternary center, and represents the first successful application of an enantioselective organomediated Diels-Alder reaction in total synthesis.