Abstract
The Wittig reaction of (−)-α-ionone (VIa) with carbethoxymethylenetriphenylphosphorane afforded (−)-ethyl α-ionylideneacetate (VIIa). tert-Butyl chromate oxidation of the above ester (VIIa) gave (−)-ethyl 4′-keto-α-ionylideneacetate (VIlla). Selenium dioxide oxidation of (−)-α-ionone (IVa) in ethanol afforded (−)-1′-hydroxy-α-ionone (X), which reacted with car-bethoxymethylenetriphenylphosphorane to give (−)-ethyl 1′-hydroxy-α-ionylideneacetate (XI). tert-Butyl chromate oxidation of the hydroxy-ester (XI) gave (−)-ethyl abscisate (XII) and ethyl 3′-keto-β-ionylideneacetate (XIII). The sensitized photooxidation of ethyl dehydro-β-ionylideneacetate (XVI) using chlorophyll was attempted.
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