Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3963-3968.DOI: 10.6023/cjoc202007052 Previous Articles     Next Articles

Special Issue: 创刊四十周年专辑



杨小会, 顾雪松, 宾怀玉, 谢建华, 周其林   

  1. 南开大学化学学院 元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2020-07-22 修回日期:2020-07-29 发布日期:2020-08-11
  • 通讯作者: 谢建华, 周其林;
  • 基金资助:

Asymmetric Synthesis of (-)-Indolizidine167B and (+)-Coniine

Yang Xiaohui, Gu Xuesong, Bin Huaiyu, Xie Jianhua, Zhou Qilin   

  1. a State Key Laboratory and Institute of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
  • Received:2020-07-22 Revised:2020-07-29 Published:2020-08-11
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21532003, 21871152, 21790332).

The enantioselective syntheses of (-)-indolizidine 167B and (+)-coniine were described based on the asymmetric hydrogenation of racemic δ-hydroxy esters via kinetic resolution. With optically active chiral δ-hydroxy ester (S)-4 and chiral 1,5-diol (R)-5 obtained by asymmetric hydrogenation of racemic ethyl 5-hydroxyoctanoate (rac-4) with chiral spiro iridium catalyst Ir-(R)-SpiroPAP as chiral starting materials, the efficient enantioselective syntheses of (-)-indolizidine 167B and (+)-coniine were achieved by using intramolecular reductive amination and N-substitution/cyclization, respectively, as a key step to construct the chiral aza-bicyclic[4.3.0]nonane skeleton and chiral piperidine ring. This provides new efficient methods for enantioselective syntheses of indolizidine and piperidine alkaloids.

Key words: alkaloids, asymmetric hydrogenation, indolizidine, coniine, reductive amination