A convenient synthesis of deuterated leukotriene A₄ methyl ester

Abstract

2,2,3,3-[2H4]-l-Iodopentane (8b) was prepared in four steps @m pmpargVr alcohol and used in the C-alkylation of the THP-protected 3-butyne-1-01 (10). Subsequent protective p u p removal of Ilb, semideuteidon of the acetylenic alcohol 126, and further @ansformation by known methods afforded the labelled key reagent 3,4,6,6, 7, 7-[2H~-(Z)-(3-nonen-l-yl)tiphenylphosphonium iodide ( 3 ) . Wnig olefination of epoq dienal 2 with the ylide generated from 3 completed the convenient synthesis of hexndeuterated leukotiene A4 methyl ester (lb).