11-脱氧-11,13(18)-二烯甘草萜醇的合成工艺改进

Improvement of preparation technology of heterocyclic diene derivative of glycyrrhetol

目的对甘草萜醇类共轭烯衍生物—11-脱氧-11,13(18)-二烯甘草萜醇的合成工艺进行优化及结构表征。方法以甘草次酸为原料,分别用红铝和硼氢化钠-碘体系进行还原修饰制得目标化合物,对2种方法的工艺和产率进行考察;用常规的四大光谱法确定化学结构。结果用红铝经两步反应制得目标化合物的总产率为29%;用硼氢化钠-碘体系还原可用一步制得目标产物,产率达65%。经第2种方法简化了操作流程,优化了纯化工艺;详细描述了目标化合物的光谱特征和理化性质。结论用硼氢化钠-碘体系还原制备11-脱氧-11,13(18-)二烯甘草萜醇的操作简单,产率高,是制备甘草萜醇类共轭双烯衍生物的较好途径。

Objective To prepare and characterize the heterocyclic diene derivative-11-deoxo-11,13(18) diene-glycyrrhetol,and optimize the preparation technology.Methods Glycyrrhetinic acid was used as starting compound;two different reduction system-red-al and sodium borohydride/iodine system were respectively used for reductive modification,the procedure of technology and the production yields of the reaction were compared;the routine spectrometric methods were used for chemical structure elucidation.Results The total yield of target compound obtained by two steps with red-al reduction system was 35%;however,the yield obtained by one step within sodium borohydride-iodine system was 65%,with a simplified operation and optimized purification process.Furthermore,the spectrometric characteristics and physicochemical properties of target compound and intermediate products were systematically described.Conclusion The technology of preparation of target compound by sodium borohydride/iodine reduction system was an effective method with advantages such as higher yield,and simplified synthesis and purification procedures.This is a feasible method for preparing heterocyclic diene derivatives of glycyrrhetol.