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Steroids, XLIV. Neighbouring group participation, XI. Decomposition of 2‐amidomethylene‐3‐hydroxysteroids
Author(s) -
Vincze Irén,
Somlai Csaba,
Schneider Gyula
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101181
Subject(s) - chemistry , decomposition , derivative (finance) , orthoester , stereochemistry , medicinal chemistry , alkyl , sodium , transformation (genetics) , group (periodic table) , organic chemistry , biochemistry , financial economics , economics , gene
During reduction with sodium tetrahydroborate the 2‐[acetyl‐(alkyl)aminomethylene]‐3‐keto steroids 1aa, ba and 2aa – ca undergo transformation into the 2,4‐diene‐2‐aldehydes 5a and 6 , respectively. These compounds are the decomposition products of the cyclic orthoester amides of the type 4a, b , formed by NAc‐6 neighbouring group participation from the 3‐hydroxy derivative A , which cannot be isolated.