Stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol

Martina De Angelis; Ludovica Primitivo; Claudia Lucarini; Sonia Agostinelli; Carla Sappino; Alessandra Ricelli; Giuliana Righi

doi:10.1016/j.carres.2020.108028

Stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol

Carbohydr Res. 2020 Jun:492:108028. doi: 10.1016/j.carres.2020.108028. Epub 2020 May 1.

Authors

Martina De Angelis¹, Ludovica Primitivo², Claudia Lucarini², Sonia Agostinelli², Carla Sappino², Alessandra Ricelli³, Giuliana Righi⁴

Affiliations

¹ "Sapienza" University of Rome, Dep. Chemistry, P.le A. Moro 5, 00185, Roma, Italy. Electronic address: m.deangelis@uniroma1.it.
² "Sapienza" University of Rome, Dep. Chemistry, P.le A. Moro 5, 00185, Roma, Italy.
³ CNR-IBPM, "Sapienza" University of Rome, Dep. Chemistry, P.le A. Moro 5, 00185, Rome, Italy.
⁴ CNR-IBPM, "Sapienza" University of Rome, Dep. Chemistry, P.le A. Moro 5, 00185, Rome, Italy. Electronic address: giuliana.righi@cnr.it.

PMID: 32413728
DOI: 10.1016/j.carres.2020.108028

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.

Keywords: 1,4-Dideoxy-1,4-imino-D-galactitol; 1,4-Dideoxy-1,4-imino-D-iditol; Asymmetric dihydroxylation; Iminosugars.

MeSH terms

Imino Sugars / chemical synthesis*
Imino Sugars / chemistry
Molecular Structure
Stereoisomerism

Substances

1,4-dideoxy-1,4-imino-D-iditol
Imino Sugars