The synthesis of 3β,16α,19-trihydroxyandrost-5-en-17-one

The possible significance of Δ 5-3β,19-dihydroxysteroids and their sulfates as intermediates in placental aromatization induced us to attempt the preparation of 3β,16α,19-trihydroxyandrost-5-en-17-one (VIII), which has not been available thus far. A successful chemical synthesis starting with 33-ace...

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Bibliographic Details
Published inSteroids Vol. 13; no. 6; pp. 793 - 802
Main Authors Petersen, L.P., Colás, A.E.
Format Journal Article
LanguageEnglish
Published Elsevier Inc 1969
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Summary:The possible significance of Δ 5-3β,19-dihydroxysteroids and their sulfates as intermediates in placental aromatization induced us to attempt the preparation of 3β,16α,19-trihydroxyandrost-5-en-17-one (VIII), which has not been available thus far. A successful chemical synthesis starting with 33-acetoxyandrost-5-en-17-one (I) is described in this paper. Another approach, the biological 16α-hydroxylation of 3β, 19-dihydroxyandrost-5-en-17-one (IVa) by liver microsomes from male rats or by mycelia from Streptomyces roseochromogenes, was also tried but with less satisfactory results.
ISSN:0039-128X
1878-5867
DOI:10.1016/0039-128X(69)90074-9