Photoredox-Catalyzed Radical Cyclization of Unactivated Alkene-Substituted β-Ketoesters Enabled Asymmetric Total Synthesis of Tricyclic Prostaglandin D<sub>2</sub> Metabolite Methyl Ester
Regio- and stereoselective photoredox-catalyzed cyclizations of alkene-substituted β-ketoesters have been accomplished for the synthesis of polyfunctionalized cyclopentanones. This was achieved using 2,3,5,6-tetrakis(carbazol-9-yl)-1,4-dicyanobenzene (4CzTPN) and 2,4,6-triisopropyl-thiophenol as cocatalysts under illumination of a blue-light-emitting-diode at ambient temperature. The developed chemistry was successfully applied in the enantioselective total synthesis of the tricyclic prostaglandin D<sub>2</sub> metabolite (tricyclic-PGDM) methyl ester, which was completed in 9 steps with an overall yield of 7%.
Authors
- Liu‐Yang Pu (ORCID: https://orcid.org/0000-0002-6129-7827)
- Qingkun Shang (ORCID: https://orcid.org/0000-0002-5521-0086)
- Jun Huang (ORCID: https://orcid.org/0000-0003-1861-2390)
- Zhen Jun Yang (ORCID: https://orcid.org/0000-0001-8036-934X)
- Miao Xiao (ORCID: https://orcid.org/0000-0002-4072-8106)
- Lei Zhu (ORCID: https://orcid.org/0000-0002-7870-8469)
- Zheyuan Wang
Institutions
- Army Medical University (CN)
- Peking University (CN)
- Peking University Shenzhen Hospital (CN)
- Genomics (United Kingdom) (GB)
- University of South China (CN)
Publication Details
- Journal
- JACS Au
- Published
- 2025-03-07
- DOI
- https://doi.org/10.1021/jacsau.4c01268
- Citations
- 3
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- National Natural Science Foundation of China
- University of South China
- Science and Technology Program of Hunan Province