Synthesis of a Conformationally Rigid Analogue of 2-Aminoadipic Acid Containing an 8-Azabicyclo[3.2.1]octane Skeleton

被引：8

作者：

Kubyshkin, Vladimir S. ^{[1
,3
]}

Mykhailiuk, Pavel K. ^{[1
,3
]}

Ulrich, Anne S. ^{[2
,3
]}

Komarov, Igor ^{[1
]}

机构：

[1] Kyiv Natl Taras Shevchenko Univ, Dept Chem, UA-01033 Kiev, Ukraine

[2] Forschungszentrum Karlsruhe, Karlsruhe Inst Technol, Inst Biol Grenzflachen, D-76021 Karlsruhe, Germany

[3] Univ Karlsruhe, Karlsruhe Inst Technol, Inst Organ Chem, D-76133 Karlsruhe, Germany

来源：

SYNTHESIS-STUTTGART | 2009年 / 19期

关键词：

conformational restriction; bicyclic compounds; pyrrolidines; alkylations; cyclization; D-ALPHA-AMINOADIPATE; AMINO-ACIDS; STEREOSELECTIVE-SYNTHESIS; SYNAPTIC EXCITATION; SPINAL NEURONS; DERIVATIVES;

D O I：

10.1055/s-0029-1216963

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, conformationally rigid analogue of 2-aminoadipic acid, 8-[(benzyloxy)carbonyl]-3-methylene-8-azabicyclo[3.2.1]octane-1,5-dicarboxylic acid, is synthesized from dimethyl rac-2,5-dibromohexanedioate. The key steps involve alkylation-cyclization of 1-benzyl 2,5-dimethyl pyrrolidine-1,2,5-tricarboxylate with 3-chloro-2-(chloromethyl)prop-1-ene to yield the 8-azabicyclo[3.2.1]octane skeleton.

引用

页码：3327 / 3331

页数：5

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