title: Synthesis of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
authors.forename: A S
authors.initials: AS
authors.lastname: Veleiro
authors.forename: M V
authors.initials: MV
authors.lastname: Nevado
authors.forename: M C
authors.initials: MC
authors.lastname: Monteserín
authors.forename: G
authors.initials: G
authors.lastname: Burton
mesh_terms: D000107:Acetylation; D000450:Aldosterone / Q000031:analogs & derivatives*; D006900:Hydroxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011374:Progesterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C094249:21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione; C094248:21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione; D000450:Aldosterone; D011374:Progesterone