Quick Access to Protoberberine and Tetrahydroprotoberberine Derivatives/Analogues with One-Pot Sequential Isochromenylium-Mediated Annulation

A one-pot access to the protoberberine and tetrahydroprotoberberine scaffold has been developed from easily available primary amine-functionalized o-alkynylbenzaldehydes. The core skeleton of protoberberine was afforded via in situ generation of isochromenylium by Ag­(I) catalysis, subsequent cycliz...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-09, Vol.89 (17), p.12853-12857
Main Authors: Wang, Tianyang, Feng, Donghui, Wang, Yikai, Yao, Zhu-Jun
Format: Article
Language:English
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Summary:A one-pot access to the protoberberine and tetrahydroprotoberberine scaffold has been developed from easily available primary amine-functionalized o-alkynylbenzaldehydes. The core skeleton of protoberberine was afforded via in situ generation of isochromenylium by Ag­(I) catalysis, subsequent cyclization to isoquinolinium, and final hydride reduction by a continuous operation procedure. The newly developed step-economic protocol shows excellent regio- and stereoselectivity and is capable of achieving those previously unavailable derivatives/analogues with electron-deficient substituents, providing a robust tool for medicinal investigations of protoberberines and derivatives.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01540