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 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.
Toshima
H
H
Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan. toshima@chem.agr.hokudai.ac.jp
Nara
S
S
Fujino
Y
Y
Ichihara
A
A
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
D001643:Bridged Bicyclo Compounds; D003517:Cyclopentanes; D054883:Oxylipins; C011006:jasmonic acid