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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 46期

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.

引用

页码：14120 / 14125

页数：6

共 37 条

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