有机化学 ›› 2018, Vol. 38 ›› Issue (9): 2443-2449.DOI: 10.6023/cjoc201802017 上一篇    下一篇

所属专题: 合成科学

研究论文

Hydramicromelins A,B和C母核的对映选择性合成

孙默然a,b, 代磊a,b, 杨华a,b, 刘宏民a,b, 于德泉a   

  1. a 郑州大学药学院 郑州 450001;
    b 新药创制与药物安全性评价河南省协同创新中心 郑州 450001
  • 收稿日期:2018-02-09 修回日期:2018-03-28 发布日期:2018-04-27
  • 通讯作者: 杨华, 刘宏民 E-mail:yanghua@zzu.edu.cn;liuhm@zzu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21372205,21302175)和河南省科技厅基础研究(No.132300410028)资助项目.

Enantioselective Synthesis of Core Structures of Hydramicromelins A, B and C

Sun Morana,b, Dai Leia,b, Yang Huaa,b, Liu Hongmina,b, Yu Dequana   

  1. a School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001;
    b Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou 450001
  • Received:2018-02-09 Revised:2018-03-28 Published:2018-04-27
  • Contact: 10.6023/cjoc201802017 E-mail:yanghua@zzu.edu.cn;liuhm@zzu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21372205, 21302175) and the Basic Research Project of Science and Technology Department of Henan Province (No. 132300410028).

Hydramicromelins A~C是具有独特化学结构和生物活性的香豆素类化合物.以本实验室发展的[2,3]-Meisenheimer重排为关键反应,以L-苯甘氨醇为起始原料,经过Wittig反应,[2,3]-Meisenheimer重排,环氧化,双羟化等7~8步反应,高收率、高对映选择性地制备出Hydramicromelins A,B和C的母核或其对映体.

关键词: Hydramicromelins A,B和C, [2,3]-Meisenheimer重排, 手性三级醇, 环氧化

Hydramicromelins A~C are coumarin compounds with unique chemical structure and biological activity. With[2,3]-Meisenheimer rearrangemen as a key reaction which has been developed in our laboratory, the core structures of Hydramicromelin A, B and C were synthesized from L-phenylglycine. The route included Wittig reaction,[2,3]-Meisenheimer rearrangement, epoxidation and dihydroxylation reaction, and it was high-yield and high-enantioselectivity.

Key words: hydramicromelins A, B and C, [2,3]-Meisenheimer rearrangement, chiral tertiary alcohol, epoxidation