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

Vladimir S. Kubyshkin; Pavel K. Mykhailiuk; Anne S. Ulrich; Igor Komarov

doi:10.1055/s-0029-1216963

PAPER

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

Vladimir S. Kubyshkin^a,c, Pavel K. Mykhailiuk*^a,c, Anne S. Ulrich^b,c, Igor Komarov^a
^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;

Abstract

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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.

Key words

conformational restriction - bicyclic compounds - pyrrolidines - alkylations - cyclization

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References

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

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