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Radiosynthesis of 1‐[ 11 C] polyhomoallylic fatty acids
Author(s) -
Channing Michael A.,
Simpson Norman
Publication year - 1993
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580330611
Subject(s) - chemistry , decarboxylation , yield (engineering) , radiosynthesis , high performance liquid chromatography , docosahexaenoic acid , organic chemistry , magnesium , chemical synthesis , fatty acid , nuclear chemistry , radiochemistry , polyunsaturated fatty acid , biochemistry , in vivo , catalysis , materials science , microbiology and biotechnology , metallurgy , biology , in vitro
A facile retro‐synthesis involving the radical chain decarboxylation of the N‐hydroxypyridine‐2‐thione esters of both arachidonic and docosahexaenoic acid was utilized to synthesize (all Z)‐1‐bromononadeca‐4,7,10,13‐tetraene, and (all Z)‐1‐bromoheneicosa‐3,6,9,12,15,18‐hexaene in 60% overall yield. The corresponding polyhomoallylic magnesium bromides were carbonated with [ 11 C]CO 2 to afford the 1‐[ 11 C]polyhomoallylic labeled fatty acids in good yield in less than 35 minutes. The final radiochemical purities were found to be in excess of 95% by radio‐HPLC.