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Über 9β, 10α‐Steroide. 3. Mitteilung [1]. Überführung von 11‐Keto‐9β, 10α‐steroiden in 10α‐Verbindungen Synthese von 10α‐Cortison, 11‐Oxo‐10α‐progesteron, 10α‐Adrenosteron und analogen 11‐Hydroxy‐Verbindungen
Author(s) -
Saucy G.,
Müller M.,
Fürst A.
Publication year - 1967
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.19670500520
Subject(s) - chemistry , isomerization , steric effects , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Isomerisation of 11‐keto‐9β, 10α( retro )‐steroids by acid or base led to the thermo‐dynamically more stable 11‐keto‐10α‐isomers, which have not yet been described in the literature. This epimerisation at C‐9 constitutes a new route for the synthesis of 10α‐steroids. The steric factors responsible for this isomerisation are discussed.