Synthesis and potato cell expansion-inducing activity of the stereochemically restricted bicyclic analogue of 7-epi-jasmonic acid

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