SESQUITERPENOID ESTERS FROM THE FRUITS OF FERULA-COMMUNIS

The fruits of the toxic variety of Ferula communis gave a series of 1-oxojaeskeanadiol esters, whose structure was established by spectroscopic data and chemical reactions, including correlation with jaeskeanadiol. Treatment of these esters with potassium hydroxide gave two polienonic products, resulting from the stepwise elimination of the ester group and one water molecule. Both compounds were unstable; the dienone underwent rapid deconjugation via a 1,5-sigmatropic hydrogen shift, whereas the trienone was oxidized in air at the terminal bond of the conjugated system. The toxic prenylated coumarins were not found in the fruits. © 1990.