4.4 Article

The spiropiperidine-3,3′-oxindole scaffold: a type II β-turn peptide isostere

Journal

TETRAHEDRON
Volume 66, Issue 25, Pages 4474-4478

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.04.077

Keywords

Peptidomimetics; Spiro compounds; Metathesis; Conformation analysis; Oxindole

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An unprecedented chiral spiropiperidine oxindole system quaternary 3-aminooxindole and relying on a ring closing acts as an highly constrained Freidinger gamma-lactam, adopting assessed by modelling and spectroscopical studies. was synthesized starting from enantiopure metathesis as the key step. This compound a type II beta-turn conformation in solution, as (C) 2010 Elsevier Ltd. All rights reserved.

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