Collective Syntheses of 8-Oxoprotoberberines via Sequential In(OTf)3-Catalyzed Cyclization and Pd(OAc)2-Catalyzed Heck Coupling

Zenghui Sun; Xinhang Zhang; Jiayue Fu; Lianjie Zhang; Maosheng Cheng; Lu Yang; Yongxiang Liu

doi:10.1021/acs.joc.3c00419

Collective Syntheses of 8-Oxoprotoberberines via Sequential In(OTf)₃-Catalyzed Cyclization and Pd(OAc)₂-Catalyzed Heck Coupling

J Org Chem. 2023 Jun 2;88(11):7179-7187. doi: 10.1021/acs.joc.3c00419. Epub 2023 May 12.

Authors

Zenghui Sun^{1

2

3}, Xinhang Zhang^{1

2

3}, Jiayue Fu^{1

2

3}, Lianjie Zhang^{1

2

3}, Maosheng Cheng^{1

3}, Lu Yang^{1

2

3}, Yongxiang Liu^{1

2

3}

Affiliations

¹ Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, P. R. China.
² Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, P. R. China.
³ Institute of Drug Research in Medicine Capital of China, Benxi 117000, P. R. China.

PMID: 37172220
DOI: 10.1021/acs.joc.3c00419

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)₃-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.