A stereodivergent approach to (-)-α-kainic acid and (+)-α-allokainic acid utilizing the complementarity of alkyne and allene cyclizations

被引：100

作者：

Chevliakov, MV ^{[1
]}

Montgomery, J ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1999年 / 121卷 / 48期

关键词：

D O I：

10.1021/ja993069j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A formal synthesis of (+)-alpha-allokainic acid and a total synthesis of (-)-alpha-kainic acid were carried out using a short, efficient, and highly stereoselective approach. From an alkyne precursor, a nickel-catalyzed cyclization and a palladium-catalyzed rearrangement were utilized in the synthesis of (+)-alpha-allokainic acid. From an allene precursor, a nickel-catalyzed cyclization was utilized in the synthesis of (-)-alpha-kainic acid. The allene cyclization used in the latter sequence was the first example of a metal-catalyzed cyclization of this type.

引用

页码：11139 / 11143

页数：5

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