A simple synthesis of 11,19-oxidosteroids.
The photochemical hypoiodination of cortisol acetonide gave a mixture of 18-iodocortisol acetonide and of the 11 beta,19-oxidoderivative. The proportion of the two products was slightly modified by the reaction temperature. Deprotection of the acetonide group of the 11 beta,19-oxidoderivative gave 11 beta,19-oxido-17 alpha,21-dihydroxy-4-pregnen-3,20-dione which led to the formation of 11 beta,19-oxido-4-androsten-3,17-dione upon treatment with sodium bismutate.
Boudi
A
A
Laboratoire de biologie hormonale, Hôpital Saint Louis, Paris, France.
Zaparucha
A
A
Galons
H
H
Chiadmi
M
M
Viossat
B
B
Tomas
A
A
Fiet
J
J
D000735:Androstenedione / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002855:Chromatography, Thin Layer; D006854:Hydrocortisone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D010083:Oxidants, Photochemical / Q000737:chemistry*; D013696:Temperature
C095750:11,19-oxido-17,21-dihydroxy-4-pregnen-3,20-dione; C095749:11,19-oxido-4-androsten-3,17-dione; D010083:Oxidants, Photochemical; C095748:cortisol acetonide; D000735:Androstenedione; D007455:Iodine; D006854:Hydrocortisone