Studies on the cannabinoid field: synthesis of new cannabinoids from 4-hydroxycoumarin and 4-hydroxythiocoumarin by pyridine-catalysed condensation of citral and citronellal

Abstract

The reaction of 4-hydroxycoumarin and 4-hydroxythiocoumarin with citral in basic as well as acidic conditions led to the formation of tetrahydrocannabiol derivatives. With citronellal, the above hydroxycoumarins afforded the corresponding hexahydrocannabiol derivatives in moderate yields. The structures and the stereochemistry of the compounds obtained are established on the basis of spectral-analytical evidence.