β-蒎烯合成抗糖尿病药物那格列奈

Synthesis of Nateglinide as an Antidiabetic Drug from β-Pinene

以β-蒎烯为原料,经过氧化、酸性重排、催化氢化、异构化得到反-4-异丙基环己基甲酸,然后转化为酰氯,再与D-苯丙氨酸发生酰化反应制得那格列奈。目标化合物经红外光谱、核磁共振氢谱、碳谱及质谱确证其化学结构。本合成方法利用天然产物为起始原料,经过六步合成了目标产物,总收率达到28.1%,合成路线简便易行,成本低廉。

Starting from β-pinene, nateglinide was synthesized through oxidation, acid-catalytic rearran-gement, hydrogenization, isomerization and acylation. The chemical structure of the target compound is confirmed by IR, IH NMR, ^13C NMR, MS. Nateglinide was successfully synthesized by using natural product as starting material, via six steps in a total yield of 28.1% with the advantages of simple operation and low cost.