Muscone is a precious fragrant compound, which is scarce in nature, many synthetic attempts for this unique natural product have been carried out. A new synthetic method for 2,15-hexadecanedione, a precursor of muscone, from imidazalium salt and di-Grignard reagent is reported. Imidazalium salt was used as tetrahydrofolate coenzyme model at formic acid oxidation level and di-Grignard reagent as nucleophile to which one-carbon unit was transferred, the biomimetic synthesis of 2,15-hexadecanedione was successfully accomplished by using the addition-hydrolysis reaction of imidazolium salt with di-Grignard reagent. A novel method for preparing muscone is provided.
麝香酮是一种珍贵的
香料化合物,自然界中含量稀少,针对这一独特
天然产物的合成尝试已有许多。报道了一种由
咪唑盐和二Grignard试剂合成
麝香酮前体2,15-十六碳二酮的新合成方法。将
咪唑盐作为
甲酸氧化
水平的四氢叶酸辅酶模型,二Grignard试剂作为接受一碳单元转移的亲核试剂,通过
咪唑盐与二Grignard试剂的加成-
水解反应成功实现了2,15-十六碳二酮的仿生合成,为
麝香酮的制备提供了一种新方法。