NMR and x‐ray conformational study of artemisiifolin and three other related germacranolides
- 18 February 2004
- journal article
- research article
- Published by Wiley in Magnetic Resonance in Chemistry
- Vol. 42 (5) , 474-483
- https://doi.org/10.1002/mrc.1352
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,4Z‐diene ring system of this compound and those of its derivatives 11,13‐dihydroartemisiifolin, isabelin and 6α‐hydroxy‐15‐oxogermacra‐1(10)E,4Z,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‐d6 solution. Copyright © 2004 John Wiley & Sons, Ltd.Keywords
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