Communication

Stereochemistry Determination by Powder X-Ray Diffraction Analysis and NMR Spectroscopy Residual Dipolar Couplings†

  1. Manuela E. García1,
  2. Silvina Pagola Dr.3,
  3. Armando Navarro-Vázquez Dr.4,
  4. Damilola D. Phillips2,
  5. Chakicherla Gayathri Dr.2,
  6. Henry Krakauer Prof.3,
  7. Peter W. Stephens Prof.5,
  8. Viviana E. Nicotra Dr.1,
  9. Roberto R. Gil Prof.2

Article first published online: 24 JUN 2009

DOI: 10.1002/anie.200900760

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 48, Issue 31, pages 5670–5674, July 20, 2009

Additional Information

How to Cite

García, M., Pagola, S., Navarro-Vázquez, A., Phillips, D., Gayathri, C., Krakauer, H., Stephens, P., Nicotra, V. and Gil, R. (2009), Stereochemistry Determination by Powder X-Ray Diffraction Analysis and NMR Spectroscopy Residual Dipolar Couplings. Angewandte Chemie International Edition, 48: 5670–5674. doi: 10.1002/anie.200900760

Author Information

  1. 1

    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) 351-4334174

  2. 2

    Department of Chemistry—Carnegie Mellon University, 4400 Fifth Ave, Pittsburgh, PA 15213 (USA), Fax: (+1) 412-268-1061

  3. 3

    Department of Physics, College of William and Mary, PO Box 8795, Williamsburg, VA 23187-8795 (USA)

  4. 4

    Departamento de Química Orgánica, Facultade de Química, Universidade de Santiago de Compostela, 15782 Santiago de Compostela (Spain)

  5. 5

    Department of Physics and Astronomy, SUNY at Stony Brook, Stony Brook, NY 11794-3800 (USA)

  1. †

    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.

Publication History

  1. Issue published online: 15 JUL 2009
  2. Article first published online: 24 JUN 2009
  3. Manuscript Revised: 4 APR 2009
  4. Manuscript Received: 9 FEB 2009

Funded by

  • NSF. Grant Number: CHE-0130903
  • DOE, Office of Basic Energy Sciences. Grant Number: DE-AC02-98CH10886
  • CONICET
  • SeCyT-UNC
  • ONR. Grant Numbers: N000140510055, N000140811235
  • Xunta de Galicia. Grant Number: PGIDIT07 PXIB 200925PR
  • spanish government. Grant Number: CTQ2007-65310

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Keywords:

  • lactols;
  • NMR spectroscopy;
  • powder X-ray diffraction;
  • residual dipolar couplings;
  • stereochemistry;
  • withanolides

Graphical Abstract

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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.

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