Syntheses of stereochemically restricted lactone-type analogues of jasmonic acids.
5-Oxa-7-epi-jasmonic acid and 5-oxa-jasmonic acid, which are stereochemically restricted lactone-type analogues of jasmonic acids, were synthesized via three-component coupling of 2(5H)-furanone, tert-butyl acetate and 1-bromo-2-pentyne. After acidic deprotection of the tert-butyl esters, the (Z)-olefin was introduced by catalytic partial reduction with the Lindlar catalyst to give the desired analogues.
Toshima
H
H
Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan. toshima@chem.agr.hokudai.ac.jp
Aramaki
H
H
Ichihara
A
A
D000085:Acetates; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D054883:Oxylipins; D010937:Plant Growth Regulators / Q000737:chemistry
D000085:Acetates; D003517:Cyclopentanes; D005663:Furans; D007202:Indicators and Reagents; D007783:Lactones; D054883:Oxylipins; D010937:Plant Growth Regulators; C011006:jasmonic acid; C089834:tert-butyl acetate