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

✍ Scribed by Martha S. Morales-Ríos; Norma F. Santos-Sánchez; Oscar R. Suárez-Castillo; Pedro Joseph-Nathan

Book ID
102525059
Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
121 KB
Volume
40
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^1^H and ^13^C 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 (^2^T~1~) and envelope‐twist (^1^E–^1^T~2~) conformations. In chloroform‐d~1~, the ^1^H 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 (^1^E–^1^T~2~) conformation populations. Copyright © 2002 John Wiley & Sons, Ltd.

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