Richardson Amie M, Chen Chun-Hsing, Snider Barry B
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
J Org Chem. 2007 Oct 12;72(21):8099-102. doi: 10.1021/jo701512w. Epub 2007 Sep 15.
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).
