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
收稿日期: 2014-08-28
修回日期: 2014-09-23
网络出版日期: 2014-09-25
基金资助
国家自然科学基金(No. 21172254)和国家高技术研究与发展计划(863计划, No. 2011AA10A202)资助项目.
Synthesis of Muricatacin and 6-Acetoxy-5-hexadecanolide Isomers from Pent-4-ynoic Acid and Hex-5-ynoic Acid
Received date: 2014-08-28
Revised date: 2014-09-23
Online published: 2014-09-25
Supported by
Project supported by the National Natural Science Foundation of China (No. 21172254) and the National Hi-Tech R&D Program of China (863 Program, No. 2011AA10A202).
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.
董宏波 , 杨明艳 , 张晓腾 , 王明安 . 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[J]. 有机化学, 2015 , 35(1) : 152 -158 . DOI: 10.6023/cjoc201408035
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 1H NMR, 13C NMR, HR-ESI-MS data and X-ray diffraction. The absolute configuration of (-)-epi-muricatacin was also ascertained by X-ray diffraction analysis.
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