Abstract
Identification of 2-(2-butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran diastereomers (4, 5) in various leaves [stinging nettle; sloe tree; strawberry; vine (Riesling); sweet silique (Bunias orientalis)] was achieved by comparison of HRGC retention and spectral (MS; vapor phase FTIR) data with those of synthetic references. Model experiments revealed their acid-catalyzed formation from 3-hydroxy-5,6-epoxy-β-ionol that was present in glycosidically bound form in the above-mentioned leaves. Assignment of the isomers 4a/4b and 5a/5b was established by NOE experiments. Enantiodifferentiation carried out by on-line coupled multidimensional gas chromatography-mass spectrometry revealed the occurrence of enantiomerically pure 5S enantiomers 4b/5b in the natural sources
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