Exploitation of the Ugi 5-Center-4-Component Reaction (U-5C-4CR) for the Generation of Diverse Libraries of Polycyclic (Spiro)Compounds

An Ugi multicomponent reaction with chiral cyclic amino acids, benzyl isocyanide and cyclic ketones (or acetone) has been exploited as key step for the generation of peptidomimetics. After a straightforward set of elaborations, the peptidomimetics were converted into polycyclic scaffolds displaying...

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Autores principales: Moni, Lisa, De Moliner, Fabio, Garbarino, Silvia, Saupe, Jörn, Mang, Christian, Basso, Andrea
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6136273/
https://www.ncbi.nlm.nih.gov/pubmed/30238002
http://dx.doi.org/10.3389/fchem.2018.00369
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author Moni, Lisa
De Moliner, Fabio
Garbarino, Silvia
Saupe, Jörn
Mang, Christian
Basso, Andrea
author_facet Moni, Lisa
De Moliner, Fabio
Garbarino, Silvia
Saupe, Jörn
Mang, Christian
Basso, Andrea
author_sort Moni, Lisa
collection PubMed
description An Ugi multicomponent reaction with chiral cyclic amino acids, benzyl isocyanide and cyclic ketones (or acetone) has been exploited as key step for the generation of peptidomimetics. After a straightforward set of elaborations, the peptidomimetics were converted into polycyclic scaffolds displaying two orthogonally protected secondary amines. Libraries of compounds were obtained decorating the molecules through acylation/reductive amination reactions on these functional groups.
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spelling pubmed-61362732018-09-20 Exploitation of the Ugi 5-Center-4-Component Reaction (U-5C-4CR) for the Generation of Diverse Libraries of Polycyclic (Spiro)Compounds Moni, Lisa De Moliner, Fabio Garbarino, Silvia Saupe, Jörn Mang, Christian Basso, Andrea Front Chem Chemistry An Ugi multicomponent reaction with chiral cyclic amino acids, benzyl isocyanide and cyclic ketones (or acetone) has been exploited as key step for the generation of peptidomimetics. After a straightforward set of elaborations, the peptidomimetics were converted into polycyclic scaffolds displaying two orthogonally protected secondary amines. Libraries of compounds were obtained decorating the molecules through acylation/reductive amination reactions on these functional groups. Frontiers Media S.A. 2018-09-06 /pmc/articles/PMC6136273/ /pubmed/30238002 http://dx.doi.org/10.3389/fchem.2018.00369 Text en Copyright © 2018 Moni, De Moliner, Garbarino, Saupe, Mang and Basso. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Moni, Lisa
De Moliner, Fabio
Garbarino, Silvia
Saupe, Jörn
Mang, Christian
Basso, Andrea
Exploitation of the Ugi 5-Center-4-Component Reaction (U-5C-4CR) for the Generation of Diverse Libraries of Polycyclic (Spiro)Compounds
title Exploitation of the Ugi 5-Center-4-Component Reaction (U-5C-4CR) for the Generation of Diverse Libraries of Polycyclic (Spiro)Compounds
title_full Exploitation of the Ugi 5-Center-4-Component Reaction (U-5C-4CR) for the Generation of Diverse Libraries of Polycyclic (Spiro)Compounds
title_fullStr Exploitation of the Ugi 5-Center-4-Component Reaction (U-5C-4CR) for the Generation of Diverse Libraries of Polycyclic (Spiro)Compounds
title_full_unstemmed Exploitation of the Ugi 5-Center-4-Component Reaction (U-5C-4CR) for the Generation of Diverse Libraries of Polycyclic (Spiro)Compounds
title_short Exploitation of the Ugi 5-Center-4-Component Reaction (U-5C-4CR) for the Generation of Diverse Libraries of Polycyclic (Spiro)Compounds
title_sort exploitation of the ugi 5-center-4-component reaction (u-5c-4cr) for the generation of diverse libraries of polycyclic (spiro)compounds
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6136273/
https://www.ncbi.nlm.nih.gov/pubmed/30238002
http://dx.doi.org/10.3389/fchem.2018.00369
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