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Collective Syntheses of 8-Oxoprotoberberines via Sequential In(OTf)-Catalyzed Cyclization and Pd(OAc)-Catalyzed Heck Coupling. | LitMetric

Collective Syntheses of 8-Oxoprotoberberines via Sequential In(OTf)-Catalyzed Cyclization and Pd(OAc)-Catalyzed Heck Coupling.

J Org Chem

Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, P. R. China.

Published: June 2023

AI Article Synopsis

Article Abstract

Six 8-oxoprotoberberines were synthesized collectively in four steps with acceptable yields (14-19%), of which the products 8-oxopalmatine, 8-oxopseudopalmatine, 8-oxoberberine, and 8-oxopseudoberberine come from nature. The synthetic route was featured with the In(OTf)-catalyzed cyclization and Heck coupling. Moreover, the syntheses of the natural products berberine, canadine, and iambertine were achieved via various reductions from 8-oxoberberine, which provided a concise approach to the syntheses of this kind of alkaloids.

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Source
http://dx.doi.org/10.1021/acs.joc.3c00419DOI Listing

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