Concise syntheses of 13-methylprotoberberine and 13-methyltetrahydroprotoberberine alkaloids

查看全文 作　　者：Wenchang [1]Chen;Xiaofen [1]Yi;Hongmin [1]Qu;Yu [1]Chen;Pei [1]Tang;Fener [1,2,3]Chen 机构地区：[1]Sichuan Research Center for Drug Precision Industrial Technology,West China School of Pharmacy,Sichuan University,Chengdu 610041,China;[2]Engineering Center of Catalysis and Synthesis for Chiral Molecules,Department of Chemistry,Fudan University,Shanghai 200433,China;[3]hanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs,Shanghai 200433,China 出　　处：《Chinese Chemical Letters》索引2022年第33卷第12期,共4页 基　　金：supported by the National Natural Science Foundation of China(No.U21A20278);Sichuan Science and Technology Program(No.2021YJ0221). 摘　　要：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. 关 键 词：13-Methylprotoberberine 13-Methyltetrahydroprotoberberine One-pot metal-free sequence Asymmetric hydrogenation