A Synthesis of (-)-cis-2-Aminomethylcyclopropanecarboxylic Acid [(-)-CAMP]

被引：12

作者：

Oikawa, Masato ^{[1
]}

Sugeno, Yuka ^{[1
]}

Ishikawa, Yuichi ^{[1
]}

Tukada, Hideyuki ^{[1
]}

机构：

[1] Yokohama City Univ, Kanazawa Ku, Yokohama, Kanagawa 2360027, Japan

来源：

SYNLETT | 2013年 / 24卷 / 07期

关键词：

amino acids; cycloaddition; photochemistry; ring contraction; stereoselective synthesis; GABA ANALOGS;

D O I：

10.1055/s-0032-1317802

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of (-)-cis-2-aminomethylcyclopropanecarboxylic acid [(-)-CAMP] has been achieved in 2.5% total yield over ten steps starting from 2-furaldehyde. The synthesis features diastereoselective cyclopropane formation via diazene, followed by oxime formation and the reduction, for construction of the gamma-aminobutyric acid (GABA) motif.

引用

页码：886 / 888

页数：3

共 15 条

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[2]

Baxendale IR, 2002, SYNLETT, P1641

[3] Resolution and conformational analysis of diastereoisomeric esters of cis- and trans-2-(aminomethyl)-1-carboxycyclopropanes [J].