Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 364-369.DOI: 10.6023/cjoc202006067 Previous Articles     Next Articles



孙默然a,b, 白磊阳a,b, 向俊鸿a,b, 杨华a,b, 于德泉a, 刘宏民a,b,*()   

  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:2020-06-29 修回日期:2020-07-23 发布日期:2020-08-18
  • 通讯作者: 刘宏民
  • 作者简介:
    * Corresponding author. E-mail:
  • 基金资助:
    国家自然科学基金(21372205); 国家自然科学基金(21302175); 河南省科技厅基础研究(132300410028)

Desymmetrization Strategy: Synthesis of Right Segment of Ingramycin

Moran Suna,b, Leiyang Baia,b, Junhong Xianga,b, Hua Yanga,b, Dequan Yua, Hongmin Liua,b,*()   

  1. a School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001
    b Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou 450001
  • Received:2020-06-29 Revised:2020-07-23 Published:2020-08-18
  • Contact: Hongmin Liu
  • Supported by:
    the National Natural Science Foundation of China(21372205); the National Natural Science Foundation of China(21302175); the Basic Research Project of Science and Technology Department of Henan Province(132300410028)

In the construction of chiral tertiary alcohol of the natural product ingramycin, the conventional asymmetric synthesis and the method that using the chiral source as material were not used. Instead, exploring the symmetry of natural product itself, the symmetric nonchiral precursor was synthesized firstly, and then the selective ester hydrolysis reaction under lipase catalysis was carried out, which not only promoted the transformation of functional groups, but also constructed a challenging and sterically congested quaternary carbon stereocenter. Based on the readily available allyl bromide and ethyl acetate, the right segment of ingramycin was synthesized by 11 steps with total yield of 26.7% and ee value of 50.84%.

Key words: ingramycin, desymmetrization, lipase, chiral tertiary alcohol