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Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline

The stereocontrolled synthesis of 1-substituted homotropanones, using chiral N-tert-butanesulfinyl imines as reaction intermediates, is described. The reaction of organolithium and Grignard reagents with hydroxy Weinreb amides, chemoselective N-tert-butanesulfinyl aldimine formation from keto aldehy...

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Detalles Bibliográficos
Autores principales: Hernández-Ibáñez, Sandra, Sirvent, Ana, Yus, Miguel, Foubelo, Francisco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10005508/
https://www.ncbi.nlm.nih.gov/pubmed/36903657
http://dx.doi.org/10.3390/molecules28052414
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author Hernández-Ibáñez, Sandra
Sirvent, Ana
Yus, Miguel
Foubelo, Francisco
author_facet Hernández-Ibáñez, Sandra
Sirvent, Ana
Yus, Miguel
Foubelo, Francisco
author_sort Hernández-Ibáñez, Sandra
collection PubMed
description The stereocontrolled synthesis of 1-substituted homotropanones, using chiral N-tert-butanesulfinyl imines as reaction intermediates, is described. The reaction of organolithium and Grignard reagents with hydroxy Weinreb amides, chemoselective N-tert-butanesulfinyl aldimine formation from keto aldehydes, decarboxylative Mannich reaction with β-keto acids of these aldimines, and organocatalyzed L-proline intramolecular Mannich cyclization are key steps of this methodology. The utility of the method was demonstrated with a synthesis of the natural product (−)-adaline, and its enantiomer, (+)-adaline.
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spelling pubmed-100055082023-03-11 Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline Hernández-Ibáñez, Sandra Sirvent, Ana Yus, Miguel Foubelo, Francisco Molecules Article The stereocontrolled synthesis of 1-substituted homotropanones, using chiral N-tert-butanesulfinyl imines as reaction intermediates, is described. The reaction of organolithium and Grignard reagents with hydroxy Weinreb amides, chemoselective N-tert-butanesulfinyl aldimine formation from keto aldehydes, decarboxylative Mannich reaction with β-keto acids of these aldimines, and organocatalyzed L-proline intramolecular Mannich cyclization are key steps of this methodology. The utility of the method was demonstrated with a synthesis of the natural product (−)-adaline, and its enantiomer, (+)-adaline. MDPI 2023-03-06 /pmc/articles/PMC10005508/ /pubmed/36903657 http://dx.doi.org/10.3390/molecules28052414 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Hernández-Ibáñez, Sandra
Sirvent, Ana
Yus, Miguel
Foubelo, Francisco
Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
title Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
title_full Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
title_fullStr Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
title_full_unstemmed Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
title_short Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
title_sort stereoselective synthesis of 1-substituted homotropanones, including natural alkaloid (−)-adaline
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10005508/
https://www.ncbi.nlm.nih.gov/pubmed/36903657
http://dx.doi.org/10.3390/molecules28052414
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