Synthesis of Methyl 1-Hydroxy-6-oxo-2-cyclohexenecarboxylate, a Component of Salicortin and Tremulacin, and the Monomer of Idesolide

We have developed a short and practical first synthesis of
methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate (2), which
has been known as a component of salicortin and tremulacin
since 1970. Birch reduction of the SEM ether of methyl
salicylate followed by oxidation of the intermediate enolate
with (−)-camphorsulfonyloxaziridine afforded the SEM enol
ether of 2. Hydrolysis of the SEM enol ether afforded 2.
We did not observe the dimerization of either racemic or
optically enriched 2 to give idesolide (1).