Stereochemistry Determination by Powder X‐Ray Diffraction Analysis and NMR Spectroscopy Residual Dipolar Couplings
2009; Wiley; Volume: 48; Issue: 31 Linguagem: Inglês
10.1002/anie.200900760
ISSN1521-3773
AutoresManuela E. García, Silvina Pagola, Armando Navarro‐Vázquez, Damilola D. Phillips, Chakicherla Gayathri, Henry Krakauer, Peter W. Stephens, Viviana E. Nicotra, Roberto R. Gil,
Tópico(s)Crystallization and Solubility Studies
ResumoAngewandte Chemie International EditionVolume 48, Issue 31 p. 5670-5674 Communication Stereochemistry Determination by Powder X-Ray Diffraction Analysis and NMR Spectroscopy Residual Dipolar Couplings† Manuela E. García, Manuela E. García Departamento de Química Orgánica and IMBIV-CONICET Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciencias Químicas II, Ciudad Universitaria, Córdoba CP 5000 (Argentina), Fax: (+54) 351-4334174Search for more papers by this authorSilvina Pagola Dr., Silvina Pagola Dr. Department of Physics, College of William and Mary, PO Box 8795, Williamsburg, VA 23187-8795 (USA)Search for more papers by this authorArmando Navarro-Vázquez Dr., Armando Navarro-Vázquez Dr. Departamento de Química Orgánica, Facultade de Química, Universidade de Santiago de Compostela, 15782 Santiago de Compostela (Spain)Search for more papers by this authorDamilola D. Phillips, Damilola D. Phillips Department of Chemistry—Carnegie Mellon University, 4400 Fifth Ave, Pittsburgh, PA 15213 (USA), Fax: (+1) 412-268-1061Search for more papers by this authorChakicherla Gayathri Dr., Chakicherla Gayathri Dr. Department of Chemistry—Carnegie Mellon University, 4400 Fifth Ave, Pittsburgh, PA 15213 (USA), Fax: (+1) 412-268-1061Search for more papers by this authorHenry Krakauer Prof., Henry Krakauer Prof. Department of Physics, College of William and Mary, PO Box 8795, Williamsburg, VA 23187-8795 (USA)Search for more papers by this authorPeter W. Stephens Prof., Peter W. Stephens Prof. Department of Physics and Astronomy, SUNY at Stony Brook, Stony Brook, NY 11794-3800 (USA)Search for more papers by this authorViviana E. Nicotra Dr., Viviana E. Nicotra Dr. vnicotra@mail.fcq.unc.edu.ar Departamento de Química Orgánica and IMBIV-CONICET Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciencias Químicas II, Ciudad Universitaria, Córdoba CP 5000 (Argentina), Fax: (+54) 351-4334174Search for more papers by this authorRoberto R. Gil Prof., Roberto R. Gil Prof. rgil@andrew.cmu.edu Department of Chemistry—Carnegie Mellon University, 4400 Fifth Ave, Pittsburgh, PA 15213 (USA), Fax: (+1) 412-268-1061Search for more papers by this author Manuela E. García, Manuela E. García Departamento de Química Orgánica and IMBIV-CONICET Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciencias Químicas II, Ciudad Universitaria, Córdoba CP 5000 (Argentina), Fax: (+54) 351-4334174Search for more papers by this authorSilvina Pagola Dr., Silvina Pagola Dr. Department of Physics, College of William and Mary, PO Box 8795, Williamsburg, VA 23187-8795 (USA)Search for more papers by this authorArmando Navarro-Vázquez Dr., Armando Navarro-Vázquez Dr. Departamento de Química Orgánica, Facultade de Química, Universidade de Santiago de Compostela, 15782 Santiago de Compostela (Spain)Search for more papers by this authorDamilola D. Phillips, Damilola D. Phillips Department of Chemistry—Carnegie Mellon University, 4400 Fifth Ave, Pittsburgh, PA 15213 (USA), Fax: (+1) 412-268-1061Search for more papers by this authorChakicherla Gayathri Dr., Chakicherla Gayathri Dr. Department of Chemistry—Carnegie Mellon University, 4400 Fifth Ave, Pittsburgh, PA 15213 (USA), Fax: (+1) 412-268-1061Search for more papers by this authorHenry Krakauer Prof., Henry Krakauer Prof. Department of Physics, College of William and Mary, PO Box 8795, Williamsburg, VA 23187-8795 (USA)Search for more papers by this authorPeter W. Stephens Prof., Peter W. Stephens Prof. Department of Physics and Astronomy, SUNY at Stony Brook, Stony Brook, NY 11794-3800 (USA)Search for more papers by this authorViviana E. Nicotra Dr., Viviana E. Nicotra Dr. vnicotra@mail.fcq.unc.edu.ar Departamento de Química Orgánica and IMBIV-CONICET Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciencias Químicas II, Ciudad Universitaria, Córdoba CP 5000 (Argentina), Fax: (+54) 351-4334174Search for more papers by this authorRoberto R. Gil Prof., Roberto R. Gil Prof. rgil@andrew.cmu.edu Department of Chemistry—Carnegie Mellon University, 4400 Fifth Ave, Pittsburgh, PA 15213 (USA), Fax: (+1) 412-268-1061Search for more papers by this author First published: 15 July 2009 https://doi.org/10.1002/anie.200900760Citations: 50 † NMR instrumentation at CMU partially supported by NSF (CHE-0130903). Use of the NSLS, BNL, was supported by DOE, Office of Basic Energy Sciences, Contract No. DE-AC02-98CH10886. S.P. thanks the College of William and Mary, Physics Dept. for funding. M.E.G. and V.E.N. thank CONICET and SeCyT-UNC for financial support. H.K. acknowledges support from ONR grants (N000140510055, N000140811235) and support for computations at the Center for Piezoelectrics by Design. A.N. thanks Centro de Supercomputación de Galicia (CESGA) for computer time, and Xunta de Galicia (PGIDIT07 PXIB 200925PR) and spanish government (CTQ2007-65310) for research grants. We thank Dr. G. E. Barboza for the collection and identification of plant material, and Prof. A. Gutierrez-Ravelo for the mass spectra. We thank Dr. N. V. Tsarevsky from ATRP Solutions for the PMMA gels. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract A matter of technique: For a new steroidal lactol, jaborosalactol 24 (1), isolated from Jaborosa parviflora, NMR spectroscopy residual dipolar couplings and powder X-ray diffraction analysis independently gave the same stereochemistry at C23–C26. Conventional NMR spectroscopic techniques, such as NOE and 3J coupling-constant analysis failed to unambiguously determine this stereochemistry. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_200900760_sm_miscellaneous_information.pdf3 MB miscellaneous information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume48, Issue31July 20, 2009Pages 5670-5674 RelatedInformation
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