Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-L-serinal

Author(s)

Kawamura, Meire Y. ; Talero, Alexander G. ; Santiago, Joao V. ; Garambel-Vilca, Edson ; Rosset, Isac G. ; Burtoloso, Antonio C. B.

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 81, n. 21, p. 10569-10575, NOV 4 2016.
• Web of Science Citations: 5

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. (AU)

• FAPESP's process: 13/26399-7 - The use of a,b-unsaturated diazoketones with Z geometry in the direct construction of functionalized indolizidine skeletons: application in the synthesis of dehydrodemethylpumiliotoxins
• Grantee: Meire Yasuko Kawamura
• Support type: Scholarships in Brazil - Master
• FAPESP's process: 13/25504-1 - Development of new methodologies for the asymmetric a-functionalization of carbonyl compounds using chiral catalysts
• Grantee: Antonio Carlos Bender Burtoloso
• Support type: Regular Research Grants
• FAPESP's process: 13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors
• Grantee: Carlos Alberto Montanari
• Support type: Research Projects - Thematic Grants