Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
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Título: | Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline |
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Autor/es: | Hernández-Ibáñez, Sandra | Sirvent, Ana | Yus, Miguel | Foubelo, Francisco |
Grupo/s de investigación o GITE: | Síntesis Asimétrica (SINTAS) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Sulfinyl imines | Decarboxylative Mannich reaction | Cyclization | Organocatalysis | Homotropanone alkaloids |
Fecha de publicación: | 6-mar-2023 |
Editor: | MDPI |
Cita bibliográfica: | Hernández-Ibáñez S, Sirvent A, Yus M, Foubelo F. Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline. Molecules. 2023; 28(5):2414. https://doi.org/10.3390/molecules28052414 |
Resumen: | 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. |
Patrocinador/es: | This research was supported by the Spanish Ministerio de Economía y Competitividad (CTQ2017-85093-P), Ministerio de Ciencia, Innovación y Universidades (RED2018-102387-T, PID2019-107268GB-100), and the University of Alicante (VIGROB-068). |
URI: | http://hdl.handle.net/10045/132745 |
ISSN: | 1420-3049 |
DOI: | 10.3390/molecules28052414 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2023 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 (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.3390/molecules28052414 |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas |
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