Tetrahedron

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

T Pathak, NF Thomas, M Akhtar, D Gani

Index: Pathak, Tanmaya; Thomas, Noel F.; Akhtar, Mahmoud; Gani, David Tetrahedron, 1990 , vol. 46, # 5 p. 1733 - 1744

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Citation Number: 16

Abstract

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.