Premium
Über Steroide. 113. Mitteilung. Zur Herstellung von 11‐Keto‐Derivaten aus im Ring C unsubstituierten Steroiden
Author(s) -
Heusler K.,
Wettstein A.
Publication year - 1953
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19530360209
Subject(s) - chemistry , androstane , stereochemistry , isomerization , ring (chemistry) , organic chemistry , catalysis
A study of the transformation of Δ 7 ‐9, 11α‐oxidosteroids into Δ 8 ‐11‐ketosteroids leads to a new two‐step process giving excellent yields. Thus Δ 8 ‐11‐ketones of the ergostane, androstane and, for the first time, also of the cholestane series are prepared. Δ 7 ‐11‐ketosteroids appear as intermediates which, according to their reactions, seem to belong to the 9β‐series. On the basis of this observation a reaction mechanism for the isomerisation of epoxides into ketones is presented.