title: 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.
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan. toshima@chem.agr.hokudai.ac.jp
authors.forename: H
authors.initials: H
authors.lastname: Toshima
authors.forename: S
authors.initials: S
authors.lastname: Nara
authors.forename: Y
authors.initials: Y
authors.lastname: Fujino
authors.forename: A
authors.initials: A
authors.lastname: Ichihara
mesh_terms: D001671:Biochemistry / Q000379:methods; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical / Q000379:methods; D054883:Oxylipins; D011198:Solanum tuberosum / Q000166:cytology / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D001643:Bridged Bicyclo Compounds; D003517:Cyclopentanes; D054883:Oxylipins; C011006:jasmonic acid