Abstract

cis- and trans-Rose oxide ketones are prepared enantioselectively using (R)-3-methylpentanedioic acid monomethyl ester as a chiral building block. All four stereoisomers of rose oxide ketone can be analysed simultaneously by enantioselective GC using heptakis-(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin in OV-1701-vi as the chiral stationary phase. The enantiomeric distribution of cis- and trans-rose oxide ketone in geranium oils of different origin was investigated and found to correlate with the enantiomeric ratios of cis- and trans-rose oxide. A pathway for the biogenesis of rose oxide ketone in Pelargonium species is proposed, including rose oxide as the precursor of rose oxide ketone. © 1997 John Wiley & Sons, Ltd.

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