Ruthenium-catalyzed alkyne-propargyl alcohol addition.: An asymmetric total synthesis of (+)-α-kainic acid

被引：58

作者：

Trost, BM ^{[1
]}

Rudd, MT ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 09期

关键词：

D O I：

10.1021/ol034241y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic A novel route to the neuroexcitatory amino acid, kainic acid, is developed. The key concept derives from a ruthenium-catalyzed cycloisomerization of a tethered alkyne-propargyl alcohol to form a cylic 2-vinyl-1-Acyl compound. A single stereocenter introduced by an asymmetric reduction of a ketone sets the stage for all the other stereocenters. A novel 1,6-addition of silyl cuprate serves to install a hydroxyl group at the diene termines.

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页码：1467 / 1470

页数：4

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