Citation: Wenchang Chen, Xiaofen Yi, Hongmin Qu, Yu Chen, Pei Tang, Fener Chen. Concise syntheses of 13-methylprotoberberine and 13-methyltetrahydroprotoberberine alkaloids[J]. Chinese Chemical Letters, ;2022, 33(12): 5080-5083. doi: 10.1016/j.cclet.2022.04.047 shu

Concise syntheses of 13-methylprotoberberine and 13-methyltetrahydroprotoberberine alkaloids

Wenchang Chen ^a ,
Xiaofen Yi ^a ,
Hongmin Qu ^a ,
Yu Chen ^a ,
Pei Tang ^{a, *,} ,
Fener Chen ^{a, b, c, *,}

a.
Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China
b.
Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China
c.
hanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China

peitang@scu.edu.cn

rfchen@fudan.edu.cn

Received Date: 14 March 2022
Revised Date: 17 April 2022
Accepted Date: 18 April 2022
Available Online: 22 April 2022

Figures(3)

The concise syntheses of eight 13-methylprotoberberine (13-MePB) and eight enantioenriched 13-methyltetrahydroprotoberberine (13-MeTHPB) alkaloids have been achieved in a tactically modular fashion. This synthetic work features a one-pot metal-free Pictet-Spengler/Friedel-Crafts hydroxyalkylation/dehydration/oxidation sequence and a following highly enantioselective Ir-catalyzed hydrogenation. Given such brevity and modularity, our developed synthetic route would be greatly beneficial to the efficient syntheses of existing natural products and new fully synthetic variants of 13-MePB and 13-MeTHPB family.
- 13-Methylprotoberberine,
- 13-Methyltetrahydroprotoberberine,
- One-pot metal-free sequence,
- Asymmetric hydrogenation
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