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1H and 13C NMR spectral assignments and conformational analysis of 14 19-nor-neoclerodane diterpenoids

✍ Scribed by Benjamín Rodríguez; María L. Jimeno

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
191 KB
Volume
42
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Unambiguous and complete assignments of ^1^H and ^13^C NMR chemical shifts for 14 19‐nor‐neoclerodane diterpenoids, nine of them isolated from natural sources and five other synthetic derivatives, are presented. The assignments are based on 2D shift‐correlated (^1^H,^1^H‐COSY, ^1^H,^13^C‐gHSQC and ^1^H,^13^C‐gHMBC) and NOE experiments. The conformations of rings A and B of these compounds are supported by the ^3^J(H,H) values and they agree with the low‐energy conformations obtained by semi‐empirical calculations. Moreover, the data obtained in this work for 2‐acetoxyteucvidin and a semisynthetic 18‐aldehyde derivative indicate that the configuration at C‐2 of the former and at C‐10 of the latter must be reversed with respect to those reported previously. Copyright © 2004 John Wiley & Sons, Ltd.

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