The total synthesis of (+)-hapalindole Q by an organomediated Diels-Alder reaction

被引:101
作者
Kinsman, AC [1 ]
Kerr, MA [1 ]
机构
[1] Univ Western Ontario, Dept Chem, London, ON N6A 5B7, Canada
关键词
D O I
10.1021/ja036191y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
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页码:14120 / 14125
页数:6
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