Synthesis of 19-functionalised derivatives of 16α-hydroxy-testosterone: mechanistic studies on oestriol biosynthesis

Abstract

The 19-hydroxy and 19-oxo derivatives of 16α,17β-dihydroxy-androst-4-en-3-one (9a) have been synthesised and shown to be intermediates in the biosynthesis of oestriol in the human placenta; O₂ is incorporated into formic acid released from C-19 of the 19-oxo compound (9b).