雄烯二酮
类固醇
睾酮(贴片)
酮
化学
内科学
内分泌学
甲基酮
立体化学
雄激素
激素
生物化学
有机化学
生物
医学
作者
Qian Mei,Douglas F. Covey
出处
期刊:Steroids
[Elsevier]
日期:2024-05-01
卷期号:205: 109391-109391
标识
DOI:10.1016/j.steroids.2024.109391
摘要
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.
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