Total Syntheses of (+)-α-Allokainic Acid and (-)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as a Chiral Auxiliary

被引：7

作者：

Liang, Yu-Fu ^{[1
]}

Chung, Chuang-Chung ^{[1
]}

Liao, De-Jhong ^{[1
]}

Lee, Woo-Jer ^{[1
]}

Tu, Yu-Wei ^{[1
]}

Uang, Biing-Jiun ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, 101 Sec 2,Kuang Fu Rd, Hsinchu 30013, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 17期

关键词：

ALPHA-AMINO-ACIDS; ASYMMETRIC MICHAEL ADDITION; KAINIC ACID; (+/-)-ALPHA-ALLOKAINIC ACID; ENANTIOSELECTIVE SYNTHESIS; HUNTINGTONS-CHOREA; ALLOKAINIC ACID; GLUTAMIC ACIDS; GLYCINE; ESTER;

D O I：

10.1021/acs.joc.8b01383

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric Michael reaction of iminoglycinate 4 to alpha,beta-unsaturated esters had been developed with >98:<2 diastereoselectivity. A reverse of diastereoselectivity for Michael reaction could be achieved by the replacement of lithium enolate with magnesium enolate. This methodology was applied to the total syntheses of (+)-alpha-allokainic acid 1 and (-)-2-epi-alpha-allokainic acid 6 each in 11 synthetic steps starting from 4 in 17.8 and 18.0% yields, respectively.

引用

页码：10564 / 10572

页数：9

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