Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1281-1289.DOI: 10.6023/cjoc201912002 Previous Articles     Next Articles

Special Issue: 有机光催化合辑


黄永康a, 解文静a, 罗永强a, 范琪琦a, 朱星亮a, 刘世领b, 施小新a   

  1. a 华东理工大学药学院 制药工程与过程化学教育部工程研究中心 上海 200237;
    b 青平药业有限公司 上海 201710
  • 收稿日期:2019-12-02 修回日期:2020-01-10 发布日期:2020-02-15
  • 通讯作者: 刘世领, 施小新;
  • 基金资助:

First Total Syntheses of 1-Benzoyl-3,4-dihydroisoquinoline Alkaloids Nelumstemine and Longifolonine Based on the Photo-oxidation

Huang Yongkanga, Xie Wenjinga, Luo Yongqianga, Fan Qiqia, Zhu Xinglianga, Liu Shilingb, Shi Xiaoxina   

  1. a Engineering Research Center of Pharmaceutical Process Chemistry of the Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai 200237;
    b Qingping Pharmaceutical Company Limited, Shanghai 201710
  • Received:2019-12-02 Revised:2020-01-10 Published:2020-02-15
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 20972048, 20172015).

A novel synthetic route for the total syntheses of 1-benzoyl-3,4-dihydroisoquinoline alkaloids was developed. Nelumstemine was synthesized for the first time via 6 steps in 50% overall yield starting from 3,4-dimethoxybenzaldehyde, and longifolonine was also synthesized for the first time via 9 steps in 35% overall yield starting from vanillin. The key step of these total syntheses is photo-oxidation of 1-benzyl-3,4-dihydroisoquinolines to 1-benzoyl-3,4-dihydroisoquinolines by air under visible-light irradiation at room temperature. The unique mild photo-oxidation of 1-benzyl-3,4-dihydro-isoquinolines has been studied in detail.

Key words: benzoyl dihydroisoquinoline alkaloids, photo-oxygenation, nelumstemine, longifolonine