Synthesis 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 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.
Veleiro
A S
AS
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
Nevado
M V
MV
Monteserín
M C
MC
Burton
G
G
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*
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