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Mycotoxin(MT81)의 합성에 관한 연구:5-carbomethoxy-2-cyclohexen-1-one
5-Carbomethoxy-2-cyclohexen-1-one(14) a key compound required for the total synthesis of the aglycone of antibacterial antibiotic Mycotoxin (MT 81) was prepared via 5 step reaction sequence using 4-cyano-cyclohexene 18 as the starting material. Thus, hydrolysis of nitrile 18 in agueous NaOH provided 3-cyclohexene carboxylic acid 19, which was iodolactonized to give bicyclic lactone 20. Dehydroiodination of iodolactone 20 with DBU gave unsaturated bicyclic lactone 21 which was hydrolyzed in methanol with K₂CO₃to furnish 5-carbomethoxy cyclohexenol 22. Swern oxidation of alcohol function of cyclohexenol 22 with DMSO and oxalyl chloride provided 5-carbomethoxy-2-cyclo-hexen-1-one (14).