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Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling

  1. Martha S. Morales-Ríos,
  2. Norma F. Santos-Sánchez,
  3. Oscar R. Suárez-Castillo,
  4. Pedro Joseph-Nathan*

Article first published online: 15 AUG 2002

DOI: 10.1002/mrc.1080

Issue

Magnetic Resonance in Chemistry

Magnetic Resonance in Chemistry

Volume 40, Issue 10, pages 677–682, October 2002

Additional Information

How to Cite

Morales-Ríos, M. S., Santos-Sánchez, N. F., Suárez-Castillo, O. R. and Joseph-Nathan, P. (2002), Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling. Magn. Reson. Chem., 40: 677–682. doi: 10.1002/mrc.1080

Author Information

  1. Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México D. F., 07000 México

*Departamento de Química, Centro de Investigación y de Estudios Avanzados, Instituto Politécnico Nacional, Apartado 14-740, México D. F., 07000 México.

Publication History

  1. Issue published online: 15 AUG 2002
  2. Article first published online: 15 AUG 2002
  3. Manuscript Accepted: 4 JUL 2002
  4. Manuscript Revised: 2 JUL 2002
  5. Manuscript Received: 16 APR 2002

Funded by

  • CONACYT.

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Keywords:

  • NMR;
  • conformation;
  • molecular modeling;
  • Flustra foliacea alkaloids

Abstract

1H and 13C NMR assignments for 1a–4a and 1b–4b were obtained using HSQC, HMBC and NOESY techniques. Differences and ambiguities from literature assignments are reconciled. For the pyrrolidine C-ring, the combined use of NMR spectroscopy and molecular mechanics calculations revealed that this ring exists in a dynamic conformational equilibrium between twist (2T1) and envelope-twist (1E–1T2) conformations. In chloroform-d1, the 1H NMR coupling constants indicate that the pyrrolidine ring is biased in favor of the envelope-twist conformation. Steric requirements of the N-prenyl group enhanced the envelope-twist (1E–1T2) conformation populations. Copyright © 2002 John Wiley & Sons, Ltd.

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