Asymmetric routes toward polyhydroxylated pyrrolidines: Synthesis of 1,4-dideoxy-1,4-imino-d-galactitol and 1,4-dideoxy-1,4-imino-d-glucitol

Carbohydr Res. 2016 Nov 29:435:100-105. doi: 10.1016/j.carres.2016.09.018. Epub 2016 Oct 3.

Abstract

Herein the total synthesis of the pyrrolidine alkaloids 1,4-dideoxy-1,4-imino-d-galactitol and its diastereoisomer 1,4-dideoxy-1,4-imino-d-glucitol is described, starting from a common optically active precursor. The key step in our approach was the double diastereoselection in the asymmetric dihydroxylation of chiral vinyl azido alcohols, obtained by means of two different regio- and stereoselective nucleophilic openings of the corresponding chiral vinyl epoxide.

Keywords: 1,4-Dideoxy-1,4-imino-d-galactitol; 1,4-Dideoxy-1,4-imino-d-glucitol; 1,4-dideoxy-1,4-imino-D-galactitol (PubChem CID: 10374754); 1,4-dideoxy-1,4-imino-D-glucitol (PubChem CID: 10877449); Asymmetric dihydroxylation; Hydroquinine 1,4-phthalazinediyl diether (PubChem CID: 45489792); Iminosugar; Osmium tetraoxide (PubChem CID: 30318); Polyhydroxylated pyrrolidines.

MeSH terms

  • Galactitol / chemistry*
  • Molecular Structure
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Sorbitol / chemistry*
  • Stereoisomerism

Substances

  • Pyrrolidines
  • Galactitol
  • Sorbitol