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NMR and x-ray conformational study of artemisiifolin and three other related germacranolides

✍ Scribed by María L. Jimeno; María del Carmen Apreda-Rojas; Félix H. Cano; Benjamín Rodríguez

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

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✦ Synopsis

Abstract

From an acetone extract of Staehelina dubia, large quantities of the previously known germacranolide artemisiifolin were isolated. The conformations of the 10‐membered germacra‐1(10)E,4__Z__‐diene ring system of this compound and those of its derivatives 11,13‐dihydroartemisiifolin, isabelin and 6α‐hydroxy‐15‐oxogermacra‐1(10)E,4__Z__,11(13)‐trien‐12,8α‐olide were studied by NMR spectroscopic methods. Low‐energy conformations were obtained by quantum mechanical calculations. An x‐ray diffraction analysis of artemisiifolin established that, in the crystalline state, it possesses a unique conformation that corresponds to the majority one existing in acetone‐d~6~ solution. Copyright © 2004 John Wiley & Sons, Ltd.

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