Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums

Authors
la Venia, Agustina; Dolensky, Bohumil; Krchnak, Viktor
Publication Year
2013
Language
English
Format
article
Status
Published version
Description
Polymer-supported N-(2-oxo-ethyl)-derivatized Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acylium ion cyclization−nucleophilic addition to yield tetrahydro-2H-oxazolo- [3,2-a]pyrazin-5(3H)-ones. The reaction conditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fully compatible with solid-phase peptide synthesis, and the products serve as conformationally constrained peptidomimetics. The traceless synthesis of bicycles is also reported as part of this work.
Fil: la Venia, Agustina. Palacký University; República Checa. University Of Notre Dame-Indiana; Estados Unidos. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Dolensky, Bohumil. Institute of Chemical Technology; República Checa
Fil: Krchnak, Viktor. Palacký University; República Checa. University Of Notre Dame-Indiana; Estados Unidos
Subject
FUSED HETEROCYCLES
IMINIUM
PEPTIDOMIMETICS
STEREOSELECTIVITY
Química Orgánica
Ciencias Químicas
CIENCIAS NATURALES Y EXACTAS
Access level
Restricted access
License
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repository
CONICET Digital (CONICET)
Institution
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identifier
oai:ri.conicet.gov.ar:11336/21577