NMR spectroscopic analysis of new spiro-piperidylrifamycins.
New spiro-piperidylrifamycin derivatives are presented. These compounds were synthesized from the reaction of 3-amino-4-iminorifamycin S and enantiomerically pure 4-piperidones, which generate diasteroisomeric rifabutin analogues with a new stereocentre at the spiranic carbon. The (1)H and (13)C NMR spectra of these new compounds, and also the configuration of the new stereogenic centres, were assigned using 2D NMR spectroscopic techniques. A preliminary study of the (1)H and (13)C NMR spectra of the starting compounds rifamycin S, 3-amino-4-iminorifamycin S and the related rifabutin was also carried out and as a result, their previously published (13)C NMR data were corrected.
Rubio
Eduardo
E
Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al CSIC, Universidad de Oviedo, C/Julián Clavería 8, 33006 Oviedo, Spain. erubio@uniovi.es
Merino
Isabel
I
García
Ana-Belén
AB
Cabal
María-Paz
MP
Ribas
Cristina
C
Bayod-Jasanada
Miguel
M
D002247:Carbon Isotopes; D009682:Magnetic Resonance Spectroscopy / Q000379:methods* / Q000592:standards*; D008968:Molecular Conformation; D009615:Nocardia / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry; D011522:Protons; D012015:Reference Standards; D017828:Rifabutin / Q000737:chemistry; D012294:Rifamycins / Q000138:chemical synthesis / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
C501220:3-amino-4-iminorifamycin S; D002247:Carbon Isotopes; D010880:Piperidines; D011522:Protons; D012294:Rifamycins; D013141:Spiro Compounds; D017828:Rifabutin; C032779:rifamycin S