Citation: Lianshun Zhang, Lan Bao, Ting Song, Shangying Qiao, Yifan Liu, Xianxiu Xu, Jinhuan Dong. Cu-catalyzed biheterocyclization along with sulfonyl remote migration: Access to Marinoquinoline alkaloids and 4-sulfonyl pyrrolo[2,3-c]quinolines[J]. Chinese Chemical Letters, ;2025, 36(10): 110915. doi: 10.1016/j.cclet.2025.110915 shu

Cu-catalyzed biheterocyclization along with sulfonyl remote migration: Access to Marinoquinoline alkaloids and 4-sulfonyl pyrrolo[2,3-c]quinolines

Lianshun Zhang ^{a, 1} ,
Lan Bao ^{b, 1} ,
Ting Song ^a ,
Shangying Qiao ^a ,
Yifan Liu ^a ,
Xianxiu Xu ^{a, *,} ,
Jinhuan Dong ^{a, *,}

a.
College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, Shandong Normal University, Ji’nan 250014, China
b.
College of Biological and Chemical Engineering, Qilu Institute of Technology, Ji’nan 250200, China

xuxx677@sdnu.edu.cn

dongjh@sdnu.edu.cn

Received Date: 26 November 2024
Revised Date: 14 January 2025
Accepted Date: 3 February 2025
Available Online: 4 February 2025

Figures(6)

The tricyclic pyrrolo[2,3-c]quinoline framework is the core structure of numerous natural products and bioactive molecules. Their syntheses usually rely on either forming middle pyridine ring by pyridannulation of 2-(1H-pyrrol-3-yl)anilines or building the pyrrole ring onto quinolines. We herein disclosed an unprecedented diheterocyclization-migration strategy for the de novo synthesis of 4-sulfonyl pyrrolo[2,3-c]quinolines from two distinct isocyanides. This methodology successively constructed the pyridine and pyrrole rings of this tricyclic scaffold in a single operation, along with remote migration of the sulfonyl group. Moreover, a collective total synthesis of alkaloids marinoquinoline A-C, H and K was accomplished by using the resulting 4-sulfonyl pyrrolo[2,3-c]quinoline as a common platform.
- Isocyanides,
- Pyrrolo[2,3-c]quinolines,
- Diheterocyclization,
- Migration,
- Collective total synthesis
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