Crystal structure of 11,18-oxidosteroids obtained by hypoiodination of cortisol acetonide.
The photochemical hypoiodination of cortisol acetonide, without neutralization of the excess of acidity during the work-up of the reaction, led to a mixture of 11 beta,18-oxido-17 alpha,21-dihydroxy-4-pregnen-3,20-dione and 11 beta,19-oxido-17 alpha,21-dihydroxy-4-pregnen-3,20-dione. Side chain cleavage of the former compound gave 11 beta,18-oxido-4-androsten-3,17-dione. The crystal structures of both of these 11 beta,18-oxidosteroids were determined by X-ray. The ring conformations are discussed and compared with those of aldosterone.
Lemoine
P
P
Faculté de pharmacie, Paris, France.
Viossat
B
B
Tomas
A
A
Boudi
A
A
Fiet
J
J
Galons
H
H
D018360:Crystallography, X-Ray; D006854:Hydrocortisone / Q000031:analogs & derivatives* / Q000378:metabolism; D007455:Iodine / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D010777:Photochemistry; D012984:Software
C095748:cortisol acetonide; D007455:Iodine; D006854:Hydrocortisone