Stereoselective synthesis of 7-substituted jasmonic acid derivatives and investigation of their biological activity

Abstract

Racemic 7-substituted derivatives of methyl jasmonate have been synthesized. Methyl 7-epi-methyljasmonate 3 was also synthesized in enantiomerically pure form in 7 steps from the Hajos–Wichert ketone 8. In addition the biological activity of the prepared compounds has been investigated for the induction of tendril coiling in Bryonia dioica and the elicitation of the phytoalexin production in Eschscholtzia californica. All the synthesized compounds showed poor activity in the bioassays. The specificity of the investigated species towards methyl 7-epi-jasmonate 1 seems to be very high.