Synthesis and absolute configuration of novel N,O-psiconucleosides using (R)-N-phenylpantolactam as a resolution agent.
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.
Camps
Pelayo
P
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
Gómez
Tània
T
Muñoz-Torrero
Diego
D
Rull
Jordi
J
Sánchez
Laura
L
Boschi
Francesca
F
Comes-Franchini
Mauro
M
Ricci
Alfredo
A
Calvet
Teresa
T
Font-Bardia
Mercè
M
Clercq
Erik De
ED
Naesens
Lieve
L
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
D000998:Antiviral Agents; D007769:Lactams; D011759:Pyrrolidines; C005412:pantolactone; D015107:4-Butyrolactone