Tetrahedron

A new route to 1, 4-diketones and its application to (z)-jasmone and dihydrojasmone synthesis

G Rosini, R Ballini, P Sorrenti

Index: Rosini, Goffredo; Ballini, Roberto; Sorrenti, Pietro Tetrahedron, 1983 , vol. 39, # 24 p. 4127 - 4132

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Citation Number: 46

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 α-nitroke= tones. Removal of protecting groups gives 1, 4-diketones which ...