Efficient preparation of 9-Z-11-methylretinal and 11-Z-11-methylretinal |
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Authors: | Prativa BS Dawadi Michiel A VerhoevenJohan Lugtenburg |
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Institution: | Leiden Institute of Chemistry, Leiden University, PO Box 9502, 2300 RA, Leiden, The Netherlands |
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Abstract: | 2-(β-Ionylidene)propyl]triphenylphosphonium bromide is reacted with 3-methyl-4-oxobut-2-enenitrile in refluxing 1,2-epoxybutane to give a mixture of 11-Z- and all-E-11-methylretinal via DIBAL-H reduction. In an analogous fashion, β-ionyl triphenylphosphonium bromide is reacted with 3,5-dimethyl-6-oxohexa-2,4-dienenitrile in 1,2-epoxybutane followed by subsequent DIBAL-H reduction to afford a mixture of new products consisting of 9-Z-11-methylretinal, its all-E isomer and 1-(2′,6′,6′-trimethylcyclohex-2′-en-1′-yl)-6-(buten-2″-al-3″-yl)-3,5-dimethylcyclohexa-1,3-diene. These molecules were obtained in pure form by HPLC. |
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Keywords: | 1-(2&prime 6&prime 6&prime -Trimethylcyclohex-2&prime -en-1&prime -yl)-6-(buten-2&Prime -al-3&Prime -yl)-3 5-dimethylcyclohexa-1 3-diene 1 4-conjugated Wittig reaction Cyclohexadiene formation |
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