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Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (-)-Adaline.

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.

SUBMITTER: Hernandez-Ibanez S 

PROVIDER: S-EPMC10005508 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (-)-Adaline.

Hernández-Ibáñez Sandra S   Sirvent Ana A   Yus Miguel M   Foubelo Francisco F  

Molecules (Basel, Switzerland) 20230306 5

The stereocontrolled synthesis of 1-substituted homotropanones, using chiral <i>N</i>-<i>tert</i>-butanesulfinyl imines as reaction intermediates, is described. The reaction of organolithium and Grignard reagents with hydroxy Weinreb amides, chemoselective <i>N</i>-<i>tert</i>-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 methodolo  ...[more]

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