Oxidation of methyl 2-trans-β-ionylideneacetate with N-bromosuccinimide afforded methyl 2-cis and trans-3'-hydroxy-β-ionylideneacetates. NaBH4 reduction of methyl 2-cis-3'-keto-β-ionylideneacetate and ethyl 4'-keto- α-ionylideneacetate gave methyl 2-cis-3'-hydrxy-β-ionylideneacetate and ethyl 4'-hydroxy-α-ionylideneacetate respectively. Further, methyl 4'-methoxy-epoxy-β-ionylideneacetate was prepared by epoxidation of methyl 4'-methoxy-β-ionylideneacetate. And then methyl 4'-hydroxy-1', 2'-dihydro-β-ionylideneacetate was synthesized from ethyl 4-keto-α-cyclogeranate. Growth inhibitory activities of the above compounds on rich seedlings were examined.
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Oritani et al. (1972) studied this question.