Novel Synthesis of a 1,3,5-Trioxazatriquinane Skeleton Using a Nitrogen Clamp

An α-hydroxyaldehyde derived from naltrexone was converted to an oxazoline dimer with ammonium chloride and sodium acetate in MeOH under reflux. The resulting dimer was treated with dl-camphorsulfonic acid in CHCl3 to give the trimer. The method for trimer synthesis was also applied to general α-hydroxyaldehydes to afford trimers in good yield.

由纳曲酮（naltrexone）衍生得到的α-羟基醛，在回流条件下于甲醇（MeOH）中与氯化铵、乙酸钠反应生成恶唑啉二聚体。所得二聚体在三氯甲烷（CHCl3）中经dl-樟脑磺酸处理后得到三聚体。该三聚体合成方法同样适用于普通α-羟基醛，可获得良好收率的对应三聚体。