Stereoselective Synthesis of Biology-Oriented Pentacyclic Pyrrolo[2,1-<i>a</i>]isoquinoline Scaffolds by Photoredox-Induced Radical Annulations
We report a visible-light photoredox-induced stereoselective radical 1,3-dipolar cycloaddition between tetrahydroisoquinolines and coumarin derivatives, providing a platform for the efficient synthesis of pseudo-natural-inspired fused pentacyclic scaffolds. Using this protocol, a diverse range of valuable fused pentacyclic pyrrolo[2,1-<i>a</i>]isoquinolines were efficiently obtained in moderate to good yields and excellent diastereoselectivities. Mechanistic investigations including radical control experiments and light on/off studies indicated that the reaction underwent a visible-light induced radical process. The insights gained from our studies are expected to advance general efforts toward the green synthesis of biology-oriented pseudo-natural products and heterocyclic skeletons.
Authors
- Ziqi Yi
- Weidong Wu (ORCID: https://orcid.org/0000-0002-5591-2221)
- Yi Xiong (ORCID: https://orcid.org/0000-0002-7640-3303)
- Chang Liu (ORCID: https://orcid.org/0000-0001-9251-708X)
- Wenhui Zhang (ORCID: https://orcid.org/0000-0003-3252-6587)
- Min Li (ORCID: https://orcid.org/0000-0003-4847-2341)
- Bing Yi (ORCID: https://orcid.org/0000-0003-2869-0691)
- Jian‐Ping Tan (ORCID: https://orcid.org/0000-0003-0386-5491)
- Yanjun Xie
Institutions
- Shanghai University of Engineering Science (CN)
- Sichuan University (CN)
- Hunan Institute of Engineering (CN)
- Green Chemistry (PL)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-26
- DOI
- https://doi.org/10.1021/acs.orglett.5c00277
- Citations
- 6
- Primary Topic
- Synthesis and Characterization of Pyrroles
- Type
- article
- Field-Weighted Citation Impact
- 5.62
Funders
- Education Department of Hunan Province
- National Natural Science Foundation of China
- Natural Science Foundation of Hunan Province
- Science and Technology Program of Hunan Province
- National College Students Innovation and Entrepreneurship Training Program