光氧化还原催化的未活化烯烃取代的β-酮酯的自由基环化反应实现了三环前列腺素D代谢物甲酯的不对称全合成。
Photoredox-Catalyzed Radical Cyclization of Unactivated Alkene-Substituted β-Ketoesters Enabled Asymmetric Total Synthesis of Tricyclic Prostaglandin D Metabolite Methyl Ester.
作者信息
Xiao Miao, Shang Qiaoli, Pu Liuyang, Wang Zheyuan, Zhu Lei, Yang Zhen, Huang Jun
机构信息
School of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China.
State Key Laboratory of Chemical Oncogenomics and Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
出版信息
JACS Au. 2025 Mar 7;5(3):1367-1375. doi: 10.1021/jacsau.4c01268. eCollection 2025 Mar 24.
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 metabolite (tricyclic-PGDM) methyl ester, which was completed in 9 steps with an overall yield of 7%.
已实现烯烃取代的β-酮酯的区域和立体选择性光氧化还原催化环化反应，用于合成多官能化环戊酮。这是在室温下，使用2,3,5,6-四（咔唑-9-基）-1,4-二氰基苯（4CzTPN）和2,4,6-三异丙基苯硫酚作为共催化剂，在蓝光发光二极管照射下实现的。所开发的化学方法成功应用于三环前列腺素D代谢物（三环-PGDM）甲酯的对映选择性全合成，该合成以9步完成，总产率为7%。
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