TY - JOUR
T1 - A unified total synthesis route to 18-trideuterated and/or 19-trideuterated testosterone, androstenedione and progesterone
AU - Qian, Mingxing
AU - Covey, Douglas F.
N1 - Publisher Copyright:
© 2024 Elsevier Inc.
PY - 2024/5
Y1 - 2024/5
N2 - 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.
AB - 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.
KW - Deuterated androstenedione
KW - Deuterated progesterone
KW - Deuterated steroids
KW - Deuterated testosterone
UR - http://www.scopus.com/inward/record.url?scp=85187020177&partnerID=8YFLogxK
U2 - 10.1016/j.steroids.2024.109391
DO - 10.1016/j.steroids.2024.109391
M3 - Article
C2 - 38437943
AN - SCOPUS:85187020177
SN - 0039-128X
VL - 205
JO - Steroids
JF - Steroids
M1 - 109391
ER -