title: Synthesis and absolute configuration of novel N,O-psiconucleosides using (R)-N-phenylpantolactam as a resolution agent.
abstract: A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2,3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.
authors.affiliation: Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia and Institut de Biomedicina, Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain. camps@ub.edu
authors.forename: Pelayo
authors.initials: P
authors.lastname: Camps
authors.forename: Tània
authors.initials: T
authors.lastname: Gómez
authors.forename: Diego
authors.initials: D
authors.lastname: Muñoz-Torrero
authors.forename: Jordi
authors.initials: J
authors.lastname: Rull
authors.forename: Laura
authors.initials: L
authors.lastname: Sánchez
authors.forename: Francesca
authors.initials: F
authors.lastname: Boschi
authors.forename: Mauro
authors.initials: M
authors.lastname: Comes-Franchini
authors.forename: Alfredo
authors.initials: A
authors.lastname: Ricci
authors.forename: Teresa
authors.initials: T
authors.lastname: Calvet
authors.forename: Mercè
authors.initials: M
authors.lastname: Font-Bardia
authors.forename: Erik De
authors.initials: ED
authors.lastname: Clercq
authors.forename: Lieve
authors.initials: L
authors.lastname: Naesens
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D004267:DNA Viruses / Q000187:drug effects* / Q000254:growth & development; D004951:Esterification; D006801:Humans; D007769:Lactams / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011759:Pyrrolidines / Q000737:chemistry; D012328:RNA Viruses / Q000187:drug effects* / Q000254:growth & development; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D000998:Antiviral Agents; D007769:Lactams; D011759:Pyrrolidines; C005412:pantolactone; D015107:4-Butyrolactone