(5S)-二氢-5-羟甲基-2(3H)-呋喃酮的一种改进合成方法

An Optimized Synthesis of(5S)-Dihydro-5-Hydroxymethyl-2(3H)-Furanone

建立了(5S)-二氢-5-羟甲基-2(3H)-呋喃酮(1)的一种改进合成方法.(R)-甘油醛缩丙酮经顺式Wittig反应、内酯化和催化氢化反应,以79%的三步总产率得到化合物1.此外,Wittig反应的反式副产物也能经催化氢化和内酯化反应转化为化合物1.本法总产率达到87%,显著优于文献方法.

An optimized synthesis of （ 5 S） - dihydro - 5 - （ hydroxymethyl ） - 2 （ 3 H ） - furanone （ 1 ） is devel- oped. （R） -2,3 -O -Isopropylidene -D -glyceraldehyde is converted to compound 1 via Z -selective Wittig olefination, laetonization and catalytic hydrogenation reactions in 79% yield for three steps. In addition, the E - byproduct of the Wittig step could also be converted to compound 1 via catalytic hydrogenation and lactonization reactions. This method provides an 87% overall yield, significantly higher than the literature method.