Synthesis of labelled [13C6]testosterone and [13C5]19-nortestosterone

Article abstract of DOI:10.1002/jlcr.2580360806

The condensation of ethyl acetoacetate-¹³C₄ and ethyl bromoacetate-¹³C₂ afforded, in seven steps, (1,2,3,4,5-¹³C₅) 5-(diethylphosphono)-2-pentanone ethylene ketal 9. The reaction of this labelled compound with 7-[[(1,1-dimethylethyl)-dimethylsilyl]oxy]-1,6,6a,7,8, 9, 9a, 9b-octahydro-6a-methyl-[6aS-(6aa,7a,9aβ,9ba)] cyclopenta[f][1]benzopyran-3 (2H)-one 13 gave the benzindenone 14 which was converted to (1,2,3,4,10,19-¹³C₆)testosterone 17 then, into (1,2,3,4,10-¹³C₅)19-nortestosterone 18 by a reductive alkylation method.