The biological formation of the 8(9)-double bond of both (4S)-(–)- and (4R)-(+)-limonenes in Mentha spicata and Citrus unshiu is found to be stereospecifically controlled by the regioselective elimination of a hydrogen atom from the 10-methyl group, i.e. the Z-methyl group, of geranyl diphosphate.
T. Suga, Y. Hiraga, M. Aihara and S. Izumi, J. Chem. Soc., Chem. Commun., 1992, 1556 DOI: 10.1039/C39920001556
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