Abstract
Requirements of the configuration at C-14 and C-13 for the aromatization of C19 steroids by human placenta have been investigated. For this puropose 14β-and 13α-androst-4-en-3-ones were synthesized as the substrate (see Chart 2). The C/D-cis-linked steroids as well as androsta-4, 14-diene-3, 17-dione were transformed into the 17-hydroxylated estrogens, when incubated with the placental 10000×g supernatant in the presence of NADPH and oxygen. The relative yield of Kober chromogens produced from these C19 steroids was found to be lower than that of androst-4-ene-3, 17-dione having normal C/D-ring juncture as listed in Table I.
