15β-hydroxysteroids (part VII). Steroids of the human perinatal period: The synthesis of steroid markers and their radioactive tracers

Abstract

We report the synthesis of 10 novel steroids obtained from 3β,15β-diacetoxy-17α-hydroxy-5-pregnen-20-one ( 1c) as intermediates in the synthesis of 15β-acetoxy-20,20-ethylenedioxy-17α-hydroxy-4-pregnen-3-one ( 6a) and its tritiated tracer 15β-acetoxy-20,20-ethylenedioxy-17α-hydroxy-1,2,6,7- 3H-pregn-4-en-3-one ( 6d). The one pot interconversion of intermediate ( 6a) to 3β,15β,17α-trihydroxy-5-pregnen-20-one ( 1a) and 3α,15β,17α-trihydroxy-5β-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 3β,15β,17α-trihydroxy-1,2,7- 3H-pregn-5-en-20-one ( 1d) and 3α,15β,17α-trihydroxy-1,2,6,7- 3H-5β-pregnan-20-one ( 2b) for the development of new immunoassays. We also report in this investigation an alternative route in the synthesis of 15β,17α-dihydroxy-4-pregnen-3,20-dione ( 7a) an intermediate in the synthesis of human 15β-hydroxysteroid metabolites.