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NMR spectroscopic analysis of new spiro‐piperidylrifamycins
Author(s) -
Rubio Eduardo,
Merino Isabel,
García AnaBelén,
Cabal MaríaPaz,
Ribas Cristina,
BayodJasanada Miguel
Publication year - 2005
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1545
Subject(s) - chemistry , stereocenter , rifabutin , carbon 13 nmr , stereochemistry , proton nmr , nmr spectra database , nuclear magnetic resonance spectroscopy , rifamycin , spectral line , organic chemistry , enantioselective synthesis , antibiotics , catalysis , biochemistry , physics , clarithromycin , astronomy
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. Copyright © 2005 John Wiley & Sons, Ltd.
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