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Keywords = homotropanone alkaloids

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16 pages, 2631 KiB  
Article
Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
by Sandra Hernández-Ibáñez, Ana Sirvent, Miguel Yus and Francisco Foubelo
Molecules 2023, 28(5), 2414; https://doi.org/10.3390/molecules28052414 - 6 Mar 2023
Cited by 3 | Viewed by 2775
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue A Journey of Organic Chemistry in Spain)
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