title: Asymmetric routes toward polyhydroxylated pyrrolidines: Synthesis of 1,4-dideoxy-1,4-imino-d-galactitol and 1,4-dideoxy-1,4-imino-d-glucitol.
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.
authors.affiliation: CNR-IBPM, "Sapienza" University of Rome, Dep. Chemistry, P.le A. Moro 5, 00185, Rome, Italy. Electronic address: giuliana.righi@cnr.it.
authors.forename: Giuliana
authors.initials: G
authors.lastname: Righi
authors.affiliation: "Sapienza" University of Rome, Dep. Chemistry, P.le A. Moro 5, 00185, Roma, Italy.
authors.forename: Emanuela
authors.initials: E
authors.lastname: Mandic'
authors.affiliation: "Sapienza" University of Rome, Dep. Chemistry, P.le A. Moro 5, 00185, Roma, Italy.
authors.forename: Carla
authors.initials: C
authors.lastname: Sappino
authors.affiliation: "Sapienza" University of Rome, Dep. Chemistry, P.le A. Moro 5, 00185, Roma, Italy.
authors.forename: Ergys
authors.initials: E
authors.lastname: Dema
authors.affiliation: CNR-IBPM, "Sapienza" University of Rome, Dep. Chemistry, P.le A. Moro 5, 00185, Rome, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Bovicelli
mesh_terms: D004376:Galactitol / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013012:Sorbitol / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D011759:Pyrrolidines; D004376:Galactitol; D013012:Sorbitol
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