Convenient syntheses of [20,20,20-H(3)]-arachidonic acid and [20,20-H(2)]-20-hydroxyeicosatetraenoic acid

Deuterated arachidonic acid and 20-HETE were prepared in good overall yields and high stereoselectivities. Key transformations include a trans-specific vinyl dibromide reduction and Suzuki cross-couplings to a lithium borate or a 9-BBN borane. These standards are three and two mass units higher, respectively, than their naturally occurring counterparts and are useful in mass spectrometry analysis.