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 fea...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.展开更多
基金supported by the National Natural Science Foundation of China(No.U21A20278)Sichuan Science and Technology Program(No.2021YJ0221).
文摘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.
