Journal of Organic Chemistry p. 4254 - 4255 (1982)
Update date:2022-08-03
Topics:
Johnson, Francis
Paul, Kenneth G.
Favara, D.
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.
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