1. Total syntheses of (+)-bernumidine and its unnatural enantiomer
- Author
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Bianca K. Correa, Cristiano Raminelli, and Tamiris R. C. Silva
- Subjects
Carbamate ,010405 organic chemistry ,Chemistry ,medicine.medical_treatment ,Organic Chemistry ,Enantioselective synthesis ,chemistry.chemical_element ,010402 general chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Kinetic resolution ,Ruthenium ,Salsolidine ,Drug Discovery ,medicine ,Organic chemistry ,Enantiomer - Abstract
Total syntheses of (+)-bernumidine and its unnatural enantiomer were accomplished through chemoenzymatic dynamic kinetic resolution and ruthenium(II)-catalyzed enantioselective hydrogenation, which provided (R)-salsolidine propyl carbamate and N-acetyl (S)-salsolidine in high yields and enantiomeric excesses, respectively. Both enantiomers of salsolidine were accessed and converted into (+)- and (−)-bernumidine via simple and efficient transformations.
- Published
- 2018
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