1. Stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol
- Author
-
Ludovica Primitivo, Martina De Angelis, Giuliana Righi, Sonia Agostinelli, Claudia Lucarini, Alessandra Ricelli, and Carla Sappino
- Subjects
Stereochemistry ,4-imino-D-galactitolAsymmetric dihydroxylation ,Iminosugars1 ,Iminosugar ,Cinchona Alkaloids ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Analytical Chemistry ,chemistry.chemical_compound ,4-Dideoxy-1 ,Iditol ,iminosugars ,1,4-Dideoxy-1,4-imino-D-galactitol ,1,4-Dideoxy-1,4-imino-D-iditol ,Asymmetric dihydroxylation ,Iminosugars ,Olefin fiber ,Molecular Structure ,010405 organic chemistry ,Chemistry ,Ligand ,Organic Chemistry ,4-imino-D-iditol1 ,Total synthesis ,Stereoisomerism ,General Medicine ,Optically active ,0104 chemical sciences ,Imino Sugars ,Dihydroxylation - Abstract
The first stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol is described. The key step in our approach was the double diastereoselection in the asymmetric dihydroxylation (AD) of suitable optically active olefin, the chiral vinyl azido alcohol 9. Performing the AD using the most common Cinchona alkaloids as ligands enabled us to identify the ligand of choice for the stereodivergent synthesis of 1,4-dideoxy-1,4-imino-D-iditol and 1,4-dideoxy-1,4-imino-D-galactitol. These type of iminosugars, both natural and unnatural, are intensively studied for their promising chemotherapeutic properties against viral infections, diabetes, cancer, and tuberculosis.
- Published
- 2020