Collect. Czech. Chem. Commun. 1990, 55, 1546-1554

Synthesis of 20-iodoeicosanoic and 20-[125I]-iodoeicosanoic acids

Jiří Protivaa, Jaroslav Peckaa, Jiří Urbanb and Jiří Zimac

a Department of Organic Chemistry, Charles University, 128 40 Prague 2
b The J. Heyrovský Institute of Physical Chemistry and Electrochemistry, Czechoslovak Academy of Sciences, 182 23 Prague 8
c Microbiological Institute, Czechoslovak Academy of Sciences, 140 00 Prague 4


20-Iodoeicosanoic acid (X) was prepared in 9 steps, its carbon chain being constructed from thiophene and ethyl ester chlorides of dodecanedioic and butanedioic acids. Isotope exchange afforded 20-[125I]-iodoeicosanoic acid required for scintigraphic studies of the myocardium. Desulfuration of the thiophene precursor VIII was accompanied by formation of side products XI-XIX arising by cleavage of the thiophene C-C bonds. Desulfuration of the model compounds XX and XXI has shown that the formation of these products is general.