Highly efficient synthesis of steroid-17-spiro-5'-oxazolidine-2',4'-diones from 17-keto steroids.
Steroids
; 55(11): 501-6, 1990 Nov.
Article
em En
| MEDLINE
| ID: mdl-2075616
ABSTRACT
Spiro[androst-4-en-17 alpha,5'-oxazolidine]-2',3,4'-trione 8a and spiro[androst-4-en-17 alpha,5'-oxazolidine]-2',3,4',11-tetraone 8b, two potentially bioactive spiranes, were prepared from the parent 17-ketones in four steps (64% and 49.5% yield, respectively). The key intermediates were the hydroxyimidates 5a and 5b, which easily underwent cyclization to the corresponding spirooxazolinone 4'-enol ethers when treated with alkylchlorocarbonates. The respective N-amyl derivatives of the spiranes 8a and 8b were obtained with n-pentyl bromide in the presence of KF. A new method for the synthesis of steroid 17 alpha-hydroxy-17-carboxyesters and 17 alpha-hydroxy-17-carboxamides is described. Attempts to synthesize the title compounds from these products were unsuccessful.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Oxazóis
/
Compostos de Espiro
/
Esteroides
/
17-Cetosteroides
Idioma:
En
Revista:
Steroids
Ano de publicação:
1990
Tipo de documento:
Article
País de afiliação:
Itália