A NEW ROUTE TO 1,4-DIKETONES AND ITS APPLICATION TO (Z)-JASMONE AND DIHYDROJASMONE SYNTHESIS.

DOI: 10.1016/S0040-4020(01)88632-4

Source and publish data:

Tetrahedron p. 4127 - 4132 (1983)

Update date:2022-08-03

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Authors:

Rosini, Goffredo

Ballini, Roberto

Sorrenti, Pietro

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Article abstract of DOI:10.1016/S0040-4020(01)88632-4

(Z)-Jasmone, dihydrojasmone and other 3-methylcyclopent-2-en-1-ones are easily synthetized 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 chainleghtening reaction followed by oxidation and denitration via p-toluenesulfonylhydrazones of the corresponding α-nitroketones.Removal of protecting groups gives 1,4-diketones which are then cyclized with alkali.

Full text of DOI:10.1016/S0040-4020(01)88632-4

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