Synthesis of [8,9,10,11-13C4]leukotriene C4

A ''one pot'' reduction of ethyl [1,2-13C2]bromoacetate with diisobutylaluminium hydride in dichloromethane, followed by reaction with triphenylphosphine, then triethylamine, yields [1,2-13C2]formylmethylenetriphenylphosphorane. Consecutive Wittig reactions of [1,2-13C2]formylmethylenetriphenylphosphorane with methyl 5(S),6(R)-epoxy-6-formylhexanoate and subsequent Wittig reactions with Z-3-nonen-1-triphenylphosphorane yields [8,9,10,11-13C4]LTA4 methyl ester, which is readily converted to [8,9,10,11-13C4]LTC4. (author)