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

Mingxing Qian, Douglas F. Covey

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Article number109391
JournalSteroids
Volume205
DOIs
StatePublished - May 2024

Keywords

  • Deuterated androstenedione
  • Deuterated progesterone
  • Deuterated steroids
  • Deuterated testosterone

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