Hernández-Ibáñez, Sandra, Sirvent, Ana, Yus, Miguel, Foubelo, Francisco
Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
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
URI: http://hdl.handle.net/10045/132745
DOI: 10.3390/molecules28052414
ISSN: 1420-3049
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.
Keywords:Sulfinyl imines, Decarboxylative Mannich reaction, Cyclization, Organocatalysis, Homotropanone alkaloids
MDPI
info:eu-repo/semantics/article