A unified total synthesis route to 18-trideuterated and/or 19-trideuterated testosterone, androstenedione and progesterone

Steroids. 2024 May:205:109391. doi: 10.1016/j.steroids.2024.109391. Epub 2024 Mar 2.


A unified total synthesis route has been used to prepare 18- and 19-trideuterated testosterone, androstenedione and progesterone. The 18-trideuterated steroid synthetic method starts with the synthesis of 2-(methyl-d3)-1,3-cyclopentanedione from CD3I and 1,3-cyclopentanedione and is subsequently converted into the Hajos-Parrish ketone for synthesis of these trideuterated steroids. The 19-trideuterated steroid synthesis proceeds through non-deuterated Hajos-Parrish ketone with incorporation of the 19-methyl-d3 group from CD3I at a later stage of the same synthetic route. Utilization of CD3I at both the initial and later stages of the synthesis provides a route to 18,19-hexadeuterated steroids. The deuterated steroids are useful for studies of steroid biosynthesis and metabolism.

Keywords: Deuterated androstenedione; Deuterated progesterone; Deuterated steroids; Deuterated testosterone.

MeSH terms

  • Androstenedione* / metabolism
  • Ketones
  • Progesterone* / metabolism
  • Steroids
  • Testosterone / metabolism


  • Androstenedione
  • Progesterone
  • Testosterone
  • Steroids
  • Ketones