Rapid Synthesis of Luotonin A Derivatives via Synergistic Visible-Light Photoredox and Acid Catalysis

Feng Wu; Wuheng Dong; Sijie Fan; Yao Yuan; Caiyun Liang; Aiyu Chen; Zuodong Yin; Zhaoguo Zhang

doi:10.1021/acs.joc.1c02617

Rapid Synthesis of Luotonin A Derivatives via Synergistic Visible-Light Photoredox and Acid Catalysis

J Org Chem. 2022 Jan 21;87(2):1302-1312. doi: 10.1021/acs.joc.1c02617. Epub 2022 Jan 11.

Authors

Feng Wu^{1

2}, Wuheng Dong³, Sijie Fan¹, Yao Yuan², Caiyun Liang³, Aiyu Chen³, Zuodong Yin¹, Zhaoguo Zhang²

Affiliations

¹ Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China.
² Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
³ Medicine Center, Guangxi University of Science and Technology, Liuzhou, Guangxi 545006, China.

PMID: 35014842
DOI: 10.1021/acs.joc.1c02617

Abstract

The merging of visible-light photoredox and acid catalysis allowed for an intramolecular Povarov cycloaddition reaction using eosin Y as the photocatalyst and TsOH·H₂O as the co-catalyst. A visible-light-promoted dehydrogenative cyclization protocol enabled the construction of Luotonin A derivatives with up to 97% yield.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyclization
Molecular Structure*
Oxidation-Reduction
Pyrroles
Quinones

Substances

Pyrroles
Quinones
luotonin A