| Full text | |
| 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: | 13/25504-1 - 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 |
| 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 |