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Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-l-serinal. 2016
Meire Y Kawamura, and
Alexánder G Talero, and
João V Santiago, and
Edson Garambel-Vilca, and
Isac G Rosset, and
Antonio C B Burtoloso
Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP, Brazil.
Highly stereoselective six-step syntheses of (-)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are described. Key transformations involve a two-step preparation of a functionalized dihydropyridin-3-one as a common intermediate followed by Luche reduction and dihydroxylation (for altro-DNJ). The same sequence employing an epoxidation/epoxide opening in place of dihydroxylation furnishes manno-DNJ.
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