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

Abstract

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.