Enantioselective Total Synthesis of (-)-α-Kainic Acid

被引：79

作者：

Farwick, Andreas ^{[1
]}

Helmchen, Guenter ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 05期

关键词：

PAUSON-KHAND REACTION; ASYMMETRIC TOTAL-SYNTHESIS; STEREOCONTROLLED TOTAL-SYNTHESIS; (-)-KAINIC ACID; KAINIC ACID; (+)-ALPHA-ALLOKAINIC ACID; RADICAL CYCLIZATION; ALLYLIC AMINATIONS; DIRECT CONVERSION; ETHERS;

D O I：

10.1021/ol1001076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective total synthesis of (-)-alpha-kainic acid is described. Key steps are an Ir-catalyzed allylic amination with a propargylic amine to provide an enyne and a diastereoselective intramolecular Pauson-Khand reaction. Subsequent steps involve a Baeyer-Villiger reaction, reduction of the resulting lactone, and direct Jones oxidation of a silyl ether.

引用

页码：1108 / 1111

页数：4

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