SYNTHESIS AND PLANT GROWTH INHIBITORY ACTIVITIES OF (+)- AND (-)-(2Z,4E)-5-(1',2'-EPOXY-2',6',6'-TRIMETHYLCYCLOHEXYL)-3-METHYL-2,4-PENTADIENOIC ACID

Article abstract of DOI:10.1016/0031-9422(83)80010-7

Chiral (+)- and (-)-enantiomers of (2Z,4E)-5-(1',2'-epoxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid have been synthesized from the chiral epoxy alcohols (+)- and (-)-1',2'-dihydro-1',2'-epoxy-β-ionone, which were prepared by Katsuki-Sharpless'asymmetric epoxidation of β-cyclogeraniol.The (+)-enantiomer showed strong inhibitory activity in a rice seedling and lettuce germination assay, whereas the (-)-enantiomer was 10³ times less active. - Key Word Index - Plant growth inhibitor; absolute configuration; relationship between enantiomers and biological activity; rice seedling growth; lettuce seed germination; abscisic acid analogue; (2Z,4E)-5-(1',2'-epoxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid.