Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione

The 21-hydroxy analogues of 11,19-oxidoprogesterone and 6,19-oxidoprogesterone have been synthesized from readily available materials. Hydroxylation at C-21 was effected with iodosobenzene (from phenyliodosodiacetate and methanolic potassium hydroxide) on a 20-ketopregnane. For the 11,19-oxido deriv...

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Detalles Bibliográficos
Autores principales: Veleiro, A.S., Nevado, M.V., Monteserín, M.C., Burton, G.
Formato: JOUR
Materias:
21-hydroxylation
oxido-bridged pregnanes
21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione
21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione
21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione
21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione
aldosterone
drug derivative
progesterone
deoxycorticosterone
mineralocorticoid receptor
unclassified drug
acetylation
article
chemical structure
chemistry
hydroxylation
oxidation reduction reaction
synthesis
drug structure
drug synthesis
steroidogenesis
Acetylation
Aldosterone
Hydroxylation
Molecular Structure
Oxidation-Reduction
Progesterone
Support, Non-U.S. Gov't
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_0039128X_v60_n3_p268_Veleiro
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario:The 21-hydroxy analogues of 11,19-oxidoprogesterone and 6,19-oxidoprogesterone have been synthesized from readily available materials. Hydroxylation at C-21 was effected with iodosobenzene (from phenyliodosodiacetate and methanolic potassium hydroxide) on a 20-ketopregnane. For the 11,19-oxido derivative, the hydroxylation was carried out on a precursor containing the oxido-bridge. This approach was not adequate for the 6,19-oxido steroid due to the very low yields encountered; hence in the latter case the order of introduction of the C-21 functionality and the oxido-bridge was reversed. © 1995.

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