title: Stereoselective synthesis and biological evaluation of D-fagomine, D-3-epi-fagomine and D-3,4-epi-fagomine analogs from D-glyceraldehyde acetonide as a common building block.
abstract: The stereoselective synthesis of D-fagomine, D-3-epi-fagomine, and D-3-epi-fagomine analogs starting from readily available D-glyceraldehyde acetonide has been achieved. The synthesis involves diastereoselective anti-vinylation of its homoallylimine, ring-closing metathesis, and stereoselective epoxidation followed by regioselective ring-opening or stereoselective dihydroxylation. The lack of a strong activity as glycosidase inhibitors of these compounds could be advantageous for their therapeutic use as chaperones.
authors.affiliation: Departamento de Catálisis y Procesos Catalíticos, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC - Universidad de Zaragoza, Pedro Cerbuna 12, E-50009 Zaragoza, Spain.
authors.forename: J Alberto
authors.initials: JA
authors.lastname: Díez
authors.forename: José A
authors.initials: JA
authors.lastname: Gálvez
authors.forename: María D
authors.initials: MD
authors.lastname: Díaz-de-Villegas
authors.forename: Ramón
authors.initials: R
authors.lastname: Badorrey
authors.forename: Barbara
authors.initials: B
authors.lastname: Bartholomew
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Nash
mesh_terms: D005985:Glyceraldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D006900:Hydroxylation; D050112:Imino Pyranoses / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D018832:Molecular Chaperones / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D050112:Imino Pyranoses; D018832:Molecular Chaperones; C459241:glyceraldehyde acetonide; D005985:Glyceraldehyde; C105643:fagomine