Citation: Huang Yongkang, Xie Wenjing, Luo Yongqiang, Fan Qiqi, Zhu Xingliang, Liu Shiling, Shi Xiaoxin. First Total Syntheses of 1-Benzoyl-3, 4-dihydroisoquinoline Alkaloids Nelumstemine and Longifolonine Based on the Photo-oxidation[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1281-1289. doi: 10.6023/cjoc201912002 shu

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

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

Corresponding author: Liu Shiling, liushiling@tenrypharm.com Shi Xiaoxin, xxshi@ecust.edu.cn
Received Date: 2 December 2019
Revised Date: 10 January 2020
Available Online: 14 February 2020
Fund Project: the National Natural Science Foundation of China 20172015Project supported by the National Natural Science Foundation of China (Nos. 20972048, 20172015)the National Natural Science Foundation of China 20972048

Figures(5)

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.
- benzoyl dihydroisoquinoline alkaloids,
- photo-oxygenation,
- nelumstemine,
- longifolonine
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