The discovery that in the steroidal compounds (6) and (15) iodine in the 19-position is smoothly displaced by reactive nucleophiles (CN–, MeSO2S–, N3–) without rearrangement was exploited in the synthesis of 19-methylthio-4-androstene-3,17-dione (14) which was shown to inhibit aromatase by co-ordination of the steroidal sulphur atom to the haem-iron of cytochrome P-450.
J. N. Wright, M. R. Calder and M. Akhtar, J. Chem. Soc., Chem. Commun., 1985, 1733 DOI: 10.1039/C39850001733
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