6,7-Dihydroxy-6,7-dihydrocanrenone isomers: improved synthesis and proton NMR study.
Steroids
; 54(1): 113-22, 1989 Jul.
Article
en En
| MEDLINE
| ID: mdl-2815155
ABSTRACT
The synthesis in improved yields of one 6,7-epoxide and three 6,7-dihydroxycanrenone derivatives is described. Canrenone was the starting material for all derivatives and was obtained by acid-catalyzed lactonization of potassium canrenoate. The epoxidation of canrenone to 6 alpha, 7 alpha-epoxycanrenone by m-chloroperbenzoic acid was improved by addition of a free radical inhibitor. This epoxide was efficiently cleaved to 6 beta, 7 alpha-dihydroxy-6,7-dihydrocanrenone by perchloric acid in a dioxane-water mixture; 6 beta, 7 beta- and 6 alpha, 7 alpha-dihydrocanrenone were obtained by OsO4 oxidation of canrenone in either-pyridine and subsequent reduction of the osmates by hydrogen sulfide. The stereochemistry of the products obtained from the reaction of osmium tetroxide with the 6,7-double bond of steroidal 4,6-dien-3-ones has been a controversial issue for some time. A detailed proton-NMR study of the three diol derivatives unequivocally confirmed the proposed stereochemical structure.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Espironolactona
Idioma:
En
Revista:
Steroids
Año:
1989
Tipo del documento:
Article
País de afiliación:
Israel