15 beta-Hydroxysteroids (Part VII). Steroids of the human perinatal period: the synthesis of steroid markers and their radioactive tracers.
We report the synthesis of 10 novel steroids obtained from 3 beta, 15 beta-diacetoxy-17 alpha-hydroxy-5-pregnen-20-one (1c) as intermediates in the synthesis of 15 beta-acetoxy-20,20-ethylenedioxy-17 alpha-hydroxy-4-pregnen-3-one (6a) and its tritiated tracer 15 beta-acetoxy-20,20-ethylenedioxy-17 alpha-hydroxy-1,2,6,7-3H-pregn-4-en-3-one (6d). The one pot interconversion of intermediate (6a) to 3 beta, 15 beta, 17 alpha-trihydroxy-5-pregnen-20-one (1a) and 3 alpha, 15 beta, 17 alpha-trihydroxy-5 beta-pregnan-20-one (2a) provides a new and efficient approach to the synthesis of diagnostically important metabolites of the human neonate and a possible route in the synthesis of the tritated tracers 3 beta, 15 beta, 17 alpha-trihydroxy-1,2,7-3H-pregn-5-en-20-one (1d) and 3 alpha, 15 beta, 17 alpha-trihydroxy-1,2,6,7-3H-5 beta-pregnan-20-one (2b) for the development of new immunoassays. We also report in this investigation an alternative route in the synthesis of 15 beta, 17 alpha-dihydroxy-4-pregnen-3,20-dione (7a) an intermediate in the synthesis of human 15 beta-hydroxysteroid metabolites.
Reeder
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Department of Metabolic Mass Spectrometry, Royal Prince Alfred Hospital, Camperdown, NSW, Australia.
Joannou
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GE
D015415:Biomarkers; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D006914:Hydroxysteroids / Q000138:chemical synthesis* / Q000378:metabolism; D007231:Infant, Newborn; D011247:Pregnancy / Q000378:metabolism*
D015415:Biomarkers; D006914:Hydroxysteroids