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Chinese Journal of Organic Chemistry >

2026 202605025

DOI: https://doi.org/10.6023/cjoc202605025

ARTICLE

Activated Methine Nitriles-Initiated Radical Polyene Cyclization for the Synthesis of Abietane-Type Tricyclic Diterpenoid Skeletons

  • Gu-Han Qin ,
  • Yan-Lin Pu ,
  • Wen Bao ,
  • Dao-Yong Zhu ,
  • Ruili Guan ,
  • Ye Zhang ,
  • Shao-Hua Wang
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  • aSchool of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou, 730000;
    bMinistry of Education Key Laboratory of Hazard Assessment and Control in Special Operational Environments, Fourth Military Medical University, Xi’an, 710032
†These authors contributed equally to this work.

Received date: 2026-05-25

  Revised date: 2026-07-23

  Online published: 2026-09-08

Supported by

National Key R&D Program of China (2023YFA1506404), the National Natural Science Foundation of China (22401123, 22501118), the Science and Technology Program of Gansu Province (23ZDFA003, 23ZDFA015, 23JRRA1028, 23CXGA0043, 24JRRA941, 24ZDFA003, 24ZD13FA017, 26JRRA175), the Lanzhou Science and Technology Planning Project (2023-QN-18, 2023-1-17, 2024-1-17), the Fundamental Research Funds for the Central Universities (lzujbky-2024-17, 2025CXZX-106, LZU-GXJJ-2025-007), the DCMST.NHC Clinical Research Project (WKZX2023CX200002).

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Abstract

Abietane-type tricyclic diterpenes, featuring a fused 6/6/6 ring system, exhibit diverse pharmacological activities and are of significant importance in drug discovery. Active methine nitriles have recently attracted considerable interest as versatile building blocks in total synthesis and medicinal chemistry due to their facile cyano-group transformations. Herein, we report a Cu(OTf)2-catalyzed polyene cyclization strategy initiated by active methine nitriles for the efficient construction of the 6/6/6 tricyclic framework. This transformation proceeds through a DTBP-mediated radical oxidation pathway, generating highly reactive intermediates that enable rapid conversion of simple acyclic polyene nitriles into complex polycyclic architectures. The method features mild conditions, broad substrate scope, good functional group tolerance, and excellent diastereoselectivity, thus offering a powerful approach to the core skeleton of abietane-type natural products and related pharmacologically relevant molecules.

Key words： polyene cyclization; active methine nitriles; radical process; 6/6/6 fused tricyclic frameworks

Cite this article

Gu-Han Qin , Yan-Lin Pu , Wen Bao , Dao-Yong Zhu , Ruili Guan , Ye Zhang , Shao-Hua Wang . Activated Methine Nitriles-Initiated Radical Polyene Cyclization for the Synthesis of Abietane-Type Tricyclic Diterpenoid Skeletons[J]. Chinese Journal of Organic Chemistry, 2026 : 202605025 . DOI: 10.6023/cjoc202605025

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