Synthesis of [4-2H2]-, (4R)[4-2H1]-and (4S)[4-2H1]- 4-(methylnitrosamino)-1 -(3′-pyridyl)-1-butanone, c-4 deuteriated isotopomers of the procarcinogen nnk

Article abstract of DOI:10.1016/S0040-4020(01)81978-5

The synthesis of C-4 dideuteriated and both C-4 monodeuteriated enantiomers of NNK, the metabolic precursor to a variety of potential carcinogens, starting from (2S)-glutamic acid and nicotinic acid is described. The route is suitable for the synthesis of NNK isotopomers labelled in each of the putative sites for metabolic activation.