Synthesis of New Optically Active 2-Pyrrolidinones

A new class of optically active 2-pyrrolidinones was synthesized, starting from S-pyroglutamic acid, a well known natural chiral synthon. The synthetic design followed led to the insertion of various substituents at positions 1 and 5 of the 2-pyrrolidinone ring, including the imidazole moiety. Some...

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Autores principales: Moutevelis-Minakakis, Panagiota, Papavassilopoulou, Eleni, Mavromoustakos, Thomas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270552/
https://www.ncbi.nlm.nih.gov/pubmed/23344188
http://dx.doi.org/10.3390/molecules18010050
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author Moutevelis-Minakakis, Panagiota
Papavassilopoulou, Eleni
Mavromoustakos, Thomas
author_facet Moutevelis-Minakakis, Panagiota
Papavassilopoulou, Eleni
Mavromoustakos, Thomas
author_sort Moutevelis-Minakakis, Panagiota
collection PubMed
description A new class of optically active 2-pyrrolidinones was synthesized, starting from S-pyroglutamic acid, a well known natural chiral synthon. The synthetic design followed led to the insertion of various substituents at positions 1 and 5 of the 2-pyrrolidinone ring, including the imidazole moiety. Some of them possess two or three stereogenic centers, the configuration of which was retained under the mild conditions used. The new compounds also carry an imidazole moiety, which, along with the 2-pyrrolidinone template, may prove pivotal to several biological processes.
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spelling pubmed-62705522018-12-14 Synthesis of New Optically Active 2-Pyrrolidinones Moutevelis-Minakakis, Panagiota Papavassilopoulou, Eleni Mavromoustakos, Thomas Molecules Article A new class of optically active 2-pyrrolidinones was synthesized, starting from S-pyroglutamic acid, a well known natural chiral synthon. The synthetic design followed led to the insertion of various substituents at positions 1 and 5 of the 2-pyrrolidinone ring, including the imidazole moiety. Some of them possess two or three stereogenic centers, the configuration of which was retained under the mild conditions used. The new compounds also carry an imidazole moiety, which, along with the 2-pyrrolidinone template, may prove pivotal to several biological processes. MDPI 2012-12-21 /pmc/articles/PMC6270552/ /pubmed/23344188 http://dx.doi.org/10.3390/molecules18010050 Text en © 2013 by the authors. licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Moutevelis-Minakakis, Panagiota
Papavassilopoulou, Eleni
Mavromoustakos, Thomas
Synthesis of New Optically Active 2-Pyrrolidinones
title Synthesis of New Optically Active 2-Pyrrolidinones
title_full Synthesis of New Optically Active 2-Pyrrolidinones
title_fullStr Synthesis of New Optically Active 2-Pyrrolidinones
title_full_unstemmed Synthesis of New Optically Active 2-Pyrrolidinones
title_short Synthesis of New Optically Active 2-Pyrrolidinones
title_sort synthesis of new optically active 2-pyrrolidinones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270552/
https://www.ncbi.nlm.nih.gov/pubmed/23344188
http://dx.doi.org/10.3390/molecules18010050
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