Total Syntheses of Asparenyn, Gobicusin B, and PPAR‐Agonist NNC 61‐4655 Through a FeCl<sub>3</sub>‐Assisted Electrophilic Fluorine‐Catalyzed 1,3‐Rearrangement of Allylic Alcohols
Abstract A FeCl 3 ‐assisted electrophilic fluorine‐catalyzed 1,3‐rearrangement was developed, characterized by its mild catalytic system and broad substrate scope. The functional group tolerance of this approach was evaluated through a series of allylic alcohols readily prepared in situ from commercially available enones. Various nucleophiles, including water, amides, and Hantzsch esters, were utilized in the reaction. A plausible mechanism was proposed to elucidate the observed transformations, and the versatility of this methodology was demonstrated through the syntheses of asparenyn, gonicusin B, and the PPAR‐agonist NNC 61‐4655.
Authors
- Hyunsoo Han (ORCID: https://orcid.org/0000-0001-7821-5851)
- Bin Lin (ORCID: https://orcid.org/0000-0003-2369-4765)
- Shunshun Yin (ORCID: https://orcid.org/0009-0008-4638-1925)
- Maosheng Cheng (ORCID: https://orcid.org/0000-0001-9073-4806)
- Shuhao Zhang (ORCID: https://orcid.org/0000-0002-4240-3815)
- Yongxiang Liu (ORCID: https://orcid.org/0000-0003-0364-0137)
- Lu Yang (ORCID: https://orcid.org/0009-0005-4778-0723)
- Hanyang Sun
Institutions
- Shenyang Pharmaceutical University (CN)
- China Institute of Veterinary Drug Control (CN)
Publication Details
- Journal
- Asian Journal of Organic Chemistry
- Published
- 2025-02-01
- DOI
- https://doi.org/10.1002/ajoc.202400716
- Citations
- 1
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.81