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).
Richardson
Amie M
AM
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Chen
Chun-Hsing
CH
Snider
Barry B
BB
D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry*; D006868:Hydrolysis; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D002264:Carboxylic Acids; D053138:Cyclohexenes; D005960:Glucosides; D013141:Spiro Compounds; C510160:idesolide; C524933:methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate; C095421:tremulacin; C113068:salicortin