Synthesis 2009(19): 3327-3331  
DOI: 10.1055/s-0029-1216963
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Vladimir S. Kubyshkina,c, Pavel K. Mykhailiuk*a,c, Anne S. Ulrichb,c, Igor Komarova
a Department of Chemistry, Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, 01033 Kyiv, Ukraine
b Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology, Forschungszentrum Karlsruhe, POB 3640, 76021 Karlsruhe, Germany
c Institut für Organische Chemie, Karlsruhe Institute of Technology, Universität Karlsruhe, Fritz-Haber-Weg 6, 76133 Karlsruhe, Germany
Fax: +380(44)2251273; e-Mail: pashamk@gmx.de;
Further Information

Publication History

Received 11 May 2009
Publication Date:
21 August 2009 (eFirst)

Abstract

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.