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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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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. |
format | Online Article Text |
id | pubmed-10005508 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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