由4-戊炔酸和5-己炔酸合成Muricatacin和6-乙酰氧基十六碳烷酸-5-内酯立体异构体  

Synthesis of Muricatacin and 6-Acetoxy-5-hexadecanolide Isomers from Pent-4-ynoic Acid and Hex-5-ynoic Acid

作　　者：董宏波[1] 杨明艳[1] 张晓腾[1] 王明安[1] 

机构地区：[1]中国农业大学应用化学系,北京100193

出　　处：《有机化学》2015年第1期152-158,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21172254);国家高技术研究与发展计划(863计划;No.2011AA10A202)资助项目~~

摘　　要：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.

关 键 词：muricatacin 6-乙酰氧基十六碳烷酸-5-内酯 Sharpless不对称双羟基化 合成 

分 类 号：O623.624[理学—有机化学]