以4-戊炔酸和5-己炔酸为原料,Sharpless不对称双羟基化反应为关键步骤,分别以6~7步反应及33.5%~54.6%的总收率合成了muricatacin和6-乙酰氧基十六碳烷酸-5-内酯的四个立体异构体.它们的化学结构得到1H NMR,13C NMR,HR-ESI-MS和X射线衍射的表征,(-)-epi-muricatacin的绝对构型通过X射线衍射予以证实.
The four isomers of 6-acetoxy-5-hexadecanolide and muricatacin were synthesized in 6~7 steps through pent- 4-ynoic acid and hex-5-ynoic acid as raw materials and Sharpless asymmetric dihydroxylation as the key step in overall yields of 33.5%~54.6%. Their structures were confirmed by 1^H NMR, 13^C NMR, HR-ESI-MS data and X-ray diffraction. The abso- lute configuration of (-)-epi-muricatacin was also ascertained by X-ray diffraction analysis.