An Efficient Synthesis of Methyl dl-cis-Jasmonate

Article abstract of DOI:10.1021/jo00143a015

An efficient synthesis of methyl dl-cis-jasmonate is described, starting from the previously described 2-(methoxycarbonyl)-3-<(methoxycarbonyl)methyl>cyclopentanone (3), itself easily prepared from succinyl chloride and methyl potassium malonate.Alkylation of 3 with 1-bromo-2-pentyne followed by selective removal of the 2-carbomethoxy group gave dehydrojasmonic acid.On esterification and reduction (H2/Pd/C/pyridine) of the triple bond to the cis olefin, dehydrojasmonic acid afforded methyl dl-cis-jasmonate in 40percent overall yield from succinyl chloride.