Synthesis and Potato Cell Expansion-inducing Activity of the Stereochemically Restricted Bicyclic Analogue of 7-Epi-jasmonic Acid

Abstract

The stereochemically restricted bicyclic analogue of 7-epi-jasmonic acid was synthesized from a known bicyclo[3.3.0]octane derivative. The enol triflate derived from the bicyclic compound was subjected to palladium-catalyzed coupling with allyltributyltin to give the desired carbon skeleton. Selective catalytic hydrogenation and subsequent acidic hydrolysis gave a new bicyclic analogue of 7-epi-jasmonic acid. The ACC conjugate of the bicyclic analogue was also synthesized. This ACC conjugate exhibited only slightly weaker potato cell expansion-inducing activity than that of the JA standard.

• 7-epi-jasmonic acid
• phytohormone
• jasmonic acid analogue
• bicyclo[3.3.0]octane