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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Frontiers Media S.A.
2018-09-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2018.00369/full |
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doaj-a7ee0e49accd4b4a9217a59cbf0da7e72020-11-25T00:45:16ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462018-09-01610.3389/fchem.2018.00369408862Exploitation of the Ugi 5-Center-4-Component Reaction (U-5C-4CR) for the Generation of Diverse Libraries of Polycyclic (Spiro)CompoundsLisa Moni0Fabio De Moliner1Silvia Garbarino2Jörn Saupe3Christian Mang4Andrea Basso5Dipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, Genova, ItalyDipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, Genova, ItalyDipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, Genova, ItalyAnalytiCon Discovery GmbH, Potsdam, GermanyAnalytiCon Discovery GmbH, Potsdam, GermanyDipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, Genova, ItalyAn 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.https://www.frontiersin.org/article/10.3389/fchem.2018.00369/fullmulticomponent reactionsdiversity oriented synthesisscaffold diversitycombinatorial librariesisocyanides |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Lisa Moni Fabio De Moliner Silvia Garbarino Jörn Saupe Christian Mang Andrea Basso |
| spellingShingle |
Lisa Moni Fabio De Moliner Silvia Garbarino Jörn Saupe Christian Mang Andrea Basso Exploitation of the Ugi 5-Center-4-Component Reaction (U-5C-4CR) for the Generation of Diverse Libraries of Polycyclic (Spiro)Compounds Frontiers in Chemistry multicomponent reactions diversity oriented synthesis scaffold diversity combinatorial libraries isocyanides |
| author_facet |
Lisa Moni Fabio De Moliner Silvia Garbarino Jörn Saupe Christian Mang Andrea Basso |
| author_sort |
Lisa Moni |
| title |
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_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_sort |
exploitation of the ugi 5-center-4-component reaction (u-5c-4cr) for the generation of diverse libraries of polycyclic (spiro)compounds |
| publisher |
Frontiers Media S.A. |
| series |
Frontiers in Chemistry |
| issn |
2296-2646 |
| publishDate |
2018-09-01 |
| 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. |
| topic |
multicomponent reactions diversity oriented synthesis scaffold diversity combinatorial libraries isocyanides |
| url |
https://www.frontiersin.org/article/10.3389/fchem.2018.00369/full |
| work_keys_str_mv |
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