有机化学 ›› 2015, Vol. 35 ›› Issue (1): 152-158.DOI: 10.6023/cjoc201408035 上一篇    下一篇

研究论文

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

董宏波, 杨明艳, 张晓腾, 王明安   

  1. 中国农业大学应用化学系 北京 100193
  • 收稿日期:2014-08-28 修回日期:2014-09-23 出版日期:2015-01-25 发布日期:2014-09-25
  • 通讯作者: 王明安 E-mail:wangma@cau.edu.cn
  • 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

Dong Hongbo, Yang Mingyan, Zhang Xiaoteng, Wang Ming'an   

  1. Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2014-08-28 Revised:2014-09-23 Online:2015-01-25 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.

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

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.

Key words: muricatacin, 6-acetoxy-5-hexadecanolide, sharpless asymmetric dihydroxylation, synthesis