Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
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Title: | Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline |
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Authors: | Hernández-Ibáñez, Sandra | Sirvent, Ana | Yus, Miguel | Foubelo, Francisco |
Research Group/s: | Síntesis Asimétrica (SINTAS) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Sulfinyl imines | Decarboxylative Mannich reaction | Cyclization | Organocatalysis | Homotropanone alkaloids |
Issue Date: | 6-Mar-2023 |
Publisher: | MDPI |
Citation: | 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 |
Abstract: | 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. |
Sponsor: | 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 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © 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/). |
Peer Review: | si |
Publisher version: | https://doi.org/10.3390/molecules28052414 |
Appears in Collections: | INV - SINTAS - Artículos de Revistas |
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File | Description | Size | Format | |
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Hernandez-Ibanez_etal_2023_Molecules.pdf | 2,63 MB | Adobe PDF | Open Preview | |
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