Efficient synthesis of carbon ‐14 labeled metabolites of the strobilurin fungicide mandestrobin using biomimetic iron‐porphyrin catalyzed oxidation

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 metabolite1. This reaction mechanism was investigated by identifying chemical structures of intermediate and by-products. Optimization of reaction factors based on the mechanism improved the yield of1 from mandestrobin up to 87%. Finally, various carbon-14 labeled metabolites of mandestrobin were prepared from1. 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 metabolite1. This reaction mechanism was investigated by identifying chemical structures of intermediate5 andp-xyloquinone derivatives6 and7, as by-products. Optimization of reaction factors based on the mechanism improved the yield of1 from mandestrobin up to 87%. Finally, various carbon-14 labeled metabolites of mandestrobin were prepared from1.

Source: Journal of Labelled Compounds and Radiopharmaceuticals - May 29, 2023 Category: Biochemistry Authors: Shuichi Murata, Motohiro Kurosawa, Takuo Fujisawa Tags: RESEARCH ARTICLE Source Type: research