有机化学 ›› 2014, Vol. 34 ›› Issue (11): 2350-2353.DOI: 10.6023/cjoc201406005 上一篇    下一篇

研究简报

3,7-二甲基-7-羟基-2-辛烯-1,6-内酯和(E)-6,7-二羟基-3,7-二甲基-2-辛烯酸的全合成

董宏波, 杨明艳, 汤博, 王明安   

  1. 中国农业大学应用化学系 北京 100193
  • 收稿日期:2014-06-05 修回日期:2014-07-02 出版日期:2014-11-25 发布日期:2014-07-15
  • 通讯作者: 王明安,wangma@cau.edu.cn E-mail:wangma@cau.edu.cn
  • 基金资助:

    “十二五”科技支撑计划(No.2011BAE06B04)和国家自然科学基金(No.21172254)资助项目.

Total Synthesis of 3,7-Dimethyl-7-hydroxy-2-octen-1,6-olide and (E)-6,7-Dihydroxy-3,7-dimethyl-2-octenic Acid

Dong Hongbo, Yang Mingyan, Tang Bo, Wang Mingan   

  1. Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2014-06-05 Revised:2014-07-02 Online:2014-11-25 Published:2014-07-15
  • Supported by:

    Project supported by the National Key Technologies R&D Program (No.2011BAE06B04) and the National Natural Science Foundation of China (No.21172254).

以甲基庚烯酮为原料经Wittig反应、水解、环氧化和分子内环化或开环等4步反应分别以6.4%和23.7%的总收率完成了天然产物3,7-二甲基-7-羟基-2-辛烯-1,6-内酯和(E)-6,7-二羟基-3,7-二甲基-2-辛烯酸的全合成, 它们的结构经1H NMR, 13C NMR和ESI-MS的确证.

关键词: 3,7-二甲基-7-羟基-2-辛烯-1,6-内酯, (E)-6, 7-二羟基-3,7-二甲基-2-辛烯酸, 全合成, 天然产物

The total synthesis of 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide and (E)-6,7-dihydroxy-3,7-dimethyl-2-octenic acid were carried out though Wittig reaction, hydrolyzation, epoxidation and intramolecular cyclization or ring-opening in overall yields of 6.4% and 23.7% using 6-methyl-5-hepten-2-one as raw materials, and their structures were characterized by 1H NMR, 13C NMR and ESI-MS spectral data.

Key words: 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide, (E)-6,7-dihydroxy-3,7-dimethyl-2-octenic acid, total synthesis, natural product