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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Kawamura, Meire Y. ; Talero, Alexander G. ; Santiago, Joao V. ; Garambel-Vilca, Edson ; Rosset, Isac G. ; Burtoloso, Antonio C. B.
Total Authors: 6
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: 13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors
Grantee:Carlos Alberto Montanari
Support type: Research Projects - Thematic Grants
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: 13/26399-7 - 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