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A conformationally restricted GABA analogue based on octahydro-1H-cyclopenta[b]pyridine scaffold

Amino Acids, ISSN: 1438-2199, Vol: 51, Issue: 2, Page: 255-261
2019
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Article Description

An approach to rel-(4aS,6R,7aR)-octahydro-1H-cyclopenta[b]pyridine-6-carboxylic acid—a bicyclic conformationally restricted γ-aminobutyric acid (GABA) analogue was developed. The eight-step sequence relied on the reaction of 2,3-bis(chloromethyl)pyridine and a C -binucleophile and the catalytic reduction of the pyridine ring as the key steps and allowed for the preparation of the title compound in 9.0% overall yield. Assessment of the octahydro-1H-cyclopenta[b]pyridine scaffold geometry showed that this template can be considered truly three-dimensional.

Bibliographic Details

Kostiantyn P. Melnykov; Oleksandr O. Grygorenko; Sergey V. Ryabukhin; Dmitriy M. Volochnyuk; Eduard B. Rusanov

Springer Science and Business Media LLC

Biochemistry, Genetics and Molecular Biology; Chemistry

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