Novel synthetic approach to non-natural conformationally rigid spiro-linked amino acids


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Resumo

1-Aminospiro[2.3]hexane-1,5-dicarboxylic and 1-ammo-5-(ammomethyl)spiro[2.3]hexane-1-carboxylic acids, which are the conformationally rigid analogues of glutamic acid and lysine, respectively, were synthesized from 3-methylidenecyclobutanecarbonitrile. The synthetic route includes a catalytic [1+2]-cycloaddition of ethyl 2-diazo-2-nitroacetate to a double bond of the unsaturated nitrile, a subsequent chemoselective reduction of the nitro and cyano groups, and a hydrolysis of the ester moiety.

Sobre autores

N. Yashin

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: elaver@org.chem.msu.ru
Rússia, Bld. 3, 1 Leninskie Gory, Moscow, 119991

N. Tikhomirova

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: elaver@org.chem.msu.ru
Rússia, Bld. 3, 1 Leninskie Gory, Moscow, 119991

K. Sedenkova

Department of Chemistry, M. V. Lomonosov Moscow State University; Institute of Physiological Active Compounds of Russian Academy of Sciences

Email: elaver@org.chem.msu.ru
Rússia, Bld. 3, 1 Leninskie Gory, Moscow, 119991; 1 Severnyi proezd, Chernogolovka, Moscow Region, 142432

D. Vasilenko

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: elaver@org.chem.msu.ru
Rússia, Bld. 3, 1 Leninskie Gory, Moscow, 119991

Yu. Grishin

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: elaver@org.chem.msu.ru
Rússia, Bld. 3, 1 Leninskie Gory, Moscow, 119991

T. Kuznetsova

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: elaver@org.chem.msu.ru
Rússia, Bld. 3, 1 Leninskie Gory, Moscow, 119991

E. Averina

Department of Chemistry, M. V. Lomonosov Moscow State University; Institute of Physiological Active Compounds of Russian Academy of Sciences

Autor responsável pela correspondência
Email: elaver@org.chem.msu.ru
Rússia, Bld. 3, 1 Leninskie Gory, Moscow, 119991; 1 Severnyi proezd, Chernogolovka, Moscow Region, 142432

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