title: Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-l-serinal.
abstract: 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.
authors: Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP, Brazil.
authors: Meire Y
authors: MY
authors: Kawamura
authors: Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP, Brazil.
authors: Alexánder G
authors: AG
authors: Talero
authors: Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP, Brazil.
authors: João V
authors: JV
authors: Santiago
authors: Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP, Brazil.
authors: Edson
authors: E
authors: Garambel-Vilca
authors: Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP, Brazil.
authors: Isac G
authors: IG
authors: Rosset
authors: Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP, Brazil.
authors: Antonio C B
authors: AC
authors: Burtoloso