The iminosugars are structural analogues of sugars in which the ring oxygen is replaced by a nitrogen atom. They are inhibitors of glycosidases and glycosyltransferases and consequently they may have a potential for therapeutic applications. Due to the difficult access to natural compounds, the synthesis of these products is of considerable interest and in particular the strategies involving open-chain precursors may allow a greater modulation in the design of analogues different structures , . In this work is reported a stereodivergent synthesis of piperidine iminosugars employing a common suitable chiral vinyl epoxy ester and a double diastereoselective asymmetric dihydroxylation , as key step. Choosing properly the Cinchona alkaloid derivatives as chiral ligands in the AD reaction, both the matched and the mismatched pathway are obtained with excellent results. Further elaborations of the diastereomeric diols obtained, allow to complete the synthesis of 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin.
Stereodivergent sinthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin by using the asymmetric dihydroxylation reaction as key step / DE ANGELIS, Martina; Agostinelli, Sonia; Centrella, Barbara; Forte, Giorgia; Lanciotti, Lucrezia; Lucarini, Claudia; . Luciani, Alessandro; Odore, Davide; Righi, Giuliana. - (2019). (Intervento presentato al convegno XLIV "A. Corbella" International Summer School on Organic Synthesis - ISOS 2019, Gargnano 9-13 Giugno 2019 tenutosi a Gargnano).
Stereodivergent sinthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin by using the asymmetric dihydroxylation reaction as key step
Martina, De Angelis
Primo
;Sonia, Agostinelli;Barbara Centrella;Lucrezia, Lanciotti;Claudia, Lucarini;Davide, Odore;
2019
Abstract
The iminosugars are structural analogues of sugars in which the ring oxygen is replaced by a nitrogen atom. They are inhibitors of glycosidases and glycosyltransferases and consequently they may have a potential for therapeutic applications. Due to the difficult access to natural compounds, the synthesis of these products is of considerable interest and in particular the strategies involving open-chain precursors may allow a greater modulation in the design of analogues different structures , . In this work is reported a stereodivergent synthesis of piperidine iminosugars employing a common suitable chiral vinyl epoxy ester and a double diastereoselective asymmetric dihydroxylation , as key step. Choosing properly the Cinchona alkaloid derivatives as chiral ligands in the AD reaction, both the matched and the mismatched pathway are obtained with excellent results. Further elaborations of the diastereomeric diols obtained, allow to complete the synthesis of 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.