A new route to 1,4 -diketones and its application to (z)-jasmone and dihydrojasmone synthesis |
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Authors: | Goffredo Rosini Roberto Ballini Pietro Sorrenti |
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Affiliation: | Dipartimento di Scienze Chimiche dell'Università Via S. Agostino n.1,62032 Camerino Italy |
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Abstract: | (Z)-Jasmone ,dihydrojasmone and other 3-methylcyclo=pent-2-en-1-ones are easily synthesized starting from aldehydes and 1-(2-methyl-1,3-dioxolane-2-yl)-2-nitroethane as reagent for 3-ketobutyl anion synthon. Nitro-aldol condensation is the chainlegthening reaction followed by oxidation and denitration via p-toluenesulfonylhydrazones of the corresponding -nitroke=tones. Removal of protecting groups gives 1,4-diketones which are then cyclized with alkali. |
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