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Efficient synthesis of carbon-14 labeled metabolites of the strobilurin fungicide mandestrobin using biomimetic iron-porphyrin catalyzed oxidation
Journal of Labelled Compounds and Radiopharmaceuticals ( IF 1.8 ) Pub Date : 2023-05-13 , DOI: 10.1002/jlcr.4044
Shuichi Murata 1 , Motohiro Kurosawa 1 , Takuo Fujisawa 1
Affiliation  

Biomimetic oxidation using synthetic iron-porphyrin (F20TPPFeCl) as a catalyst eliminated a xylene moiety of the fungicide mandestrobin, uniformly labeled with carbon-14 at the benzyl ring, to produce the corresponding radiolabeled metabolite 1. This reaction mechanism was investigated by identifying chemical structures of intermediate 5 and p-xyloquinone derivatives 6 and 7, as by-products. Optimization of reaction factors based on the mechanism improved the yield of 1 from mandestrobin up to 87%. Finally, various carbon-14 labeled metabolites of mandestrobin were prepared from 1.

中文翻译:

利用仿生铁卟啉催化氧化高效合成甲氧基丙烯酸酯类杀菌剂曼德斯特宾的碳 14 标记代谢物

使用合成铁卟啉 (F 20 TPPFeCl) 作为催化剂进行仿生氧化,消除了杀菌剂 mandestrobin 的二甲苯部分,在苄基环上均匀标记有碳 14,产生相应的放射性标记代谢物1。通过鉴定副产物中间体5对二甲苯醌衍生物67的化学结构来研究该反应机理。基于该机理优化反应因素,将曼甲肟酯1的收率提高至87%。最后,由1制备了不同碳 14 标记的 mandestrobin 代谢物。
更新日期:2023-05-13
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