A new practical method for the preparation of [3H6]-leukotrienes C4 and D4

Article abstract of DOI:10.1002/jlcr.2580360612

A new method for the synthesis of highly deuterated or tritiated leukotrienes was developed. The higher reactivity of a terminal alkene compared to a 1,2-disubstituted one permitted the selective deuteration or tritiation of the diyne 14,15,19,19,20,20-hexadehydro LTC₄ triester 1. After hydrolysis. LTC₄ was obtained in 36% overall yield. An average of seven deuterium or tritium atoms was incorporated and the specific activity of the tritiated LTC₄ was greater than 180 Ci/mmol. 1 was obtained from the addition of glutathione to 14,15,19,19,20,20-hexadehydro LTA₄ ethyl ester which was the product of a Wittig reaction between (3,8-nonanediyn-1-yl)triphenylphosphonium iodide and 5(S), 6(S), 7(E), 9(E) ethyl 5,6-epoxy-11-oxo-7,9-undecadienoate.