1. Stereodivergent synthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin
- Author
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Alessandra Ricelli, Martina De Angelis, Maria Grazia De Dominicis, Marianna D’Alessio, Paolo Mencarelli, Carla Sappino, Giuliana Righi, Sara Sannino, Emanuela Mandic, and Ludovica Primitivo
- Subjects
010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Epoxide ,Stereodivergent synthesis ,Optically active ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Biochemistry ,Iminosugars ,0104 chemical sciences ,1-deoxy-D-nojirimycin ,Nojirimycin ,chemistry.chemical_compound ,Stereospecificity ,Dihydroxylation ,1-deoxy-D-altronojirimycin ,Asymmetric dihydroxylation ,Drug Discovery ,Piperidine ,Azide - Abstract
A stereodivergent approach for producing piperidine iminosugars has been developed employing a common optically active precursor. The key steps of the synthetic pathway are the double diastereoselection in the asymmetric dihydroxylation of the suitable chiral vinyl epoxy ester and the regio- and stereospecific opening of the epoxide ring with azide. The synthesis of two piperidine iminosugars, 1-deoxy-D-altronojirimycin and 1-deoxy-D-nojirimycin, was achieved by two related routes.
- Published
- 2021