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Untersuchungen über Steroide XLII . Umwandlung des 17α‐Pseudostrophanthidins in 19‐Hydroxy‐8, 19‐epoxy‐14β, 17α‐cortexon und 8‐Hydroxy‐19‐nor‐14β, 17α‐cortexon
Author(s) -
Merkel Wolfgang,
Ehrenstein Maximilian
Publication year - 1969
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.19690520740
Subject(s) - chemistry , epoxy , anhydrous , dimethylformamide , sodium , medicinal chemistry , sodium methoxide , organic chemistry , stereochemistry , methanol , solvent
The synthesis of a structural isomer of aldosterone, viz. 19‐hydroxy‐8, 19‐epoxy‐(11‐) de(s)oxycorticosterone (= 19‐hydroxy‐8, 19‐epoxy‐cortexone), and a number of related compounds was reported earlier from this laboratory [1]. It appeared desirable to prepare the corresponding compounds of the 17α‐series also, such as 19‐hydroxy‐8, 19‐epoxy‐14 β, 17 (βH)‐deoxycorticosterone ( 28 ). 17 α‐Pseudostrophanthidin ( 2 ), which has not yet been described in the literature, was considered as starting material for the synthesis of 28. 2 has now been prepared by heating a solution of pseudostrophanthidin ( 1 ) in dimethylformamide in the presence of sodium p ‐toluenesulfonate and anhydrous sodium acetate. 2 was characterized as the 3, 19‐diacetate ( 7 ), the 19‐methylal ( 8 ) and the 3‐monoacetat ( 9 ). 9 was also obtained by acetylating the methylal 8 and demethylating the resulting reaction product 10. To support the structures assigned to 9 and, by implication, to 2 , a series of further reactions were carried out.