Concise syntheses of 13-methylprotoberb erine and 13-methyltetrahydroprotob erberine alkaloids

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/de...

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Bibliographic Details
Published inChinese chemical letters Vol. 33; no. 12; pp. 5080 - 5083
Main Authors Chen, Wenchang, Yi, Xiaofen, Qu, Hongmin, Chen, Yu, Tang, Pei, Chen, Fener
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier 01.12.2022
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
13-Methyltetrahydroprotoberberine
HYDROGENATION
One-pot metal-free sequence
ISOQUINOLINE ALKALOIDS
Asymmetric hydrogenation
13-Methylprotoberberine
MICE
DERIVATIVES
PROTOBERBERINE ALKALOIDS
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Summary: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. (c) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2022.04.047