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

N. V. Yashin; N. E. Tikhomirova; K. N. Sedenkova; D. A. Vasilenko; Yu. K. Grishin; T. S. Kuznetsova; E. B. Averina

doi:10.1007/s11172-019-2452-0

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

Authors: Yashin N.V.¹, Tikhomirova N.E.¹, Sedenkova K.N.¹^,2, Vasilenko D.A.¹, Grishin Y.K.¹, Kuznetsova T.S.¹, Averina E.B.¹^,2
Affiliations:
1. Department of Chemistry, M. V. Lomonosov Moscow State University
2. Institute of Physiological Active Compounds of Russian Academy of Sciences
Issue: Vol 68, No 3 (2019)
Pages: 547-551
Section: Full Article
URL: https://journals.rcsi.science/1066-5285/article/view/243313
DOI: https://doi.org/10.1007/s11172-019-2452-0
ID: 243313

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Abstract

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.