Synthesis of 11 alpha-hydroxyprogesterone haptens.
C-4 and C-6 bridged haptens of 11 alpha-hydroxyprogesterone, an anti-androgen, were respectively synthesized via 4, 5 and 5 alpha, 6 alpha epoxide ring openings using 3-mercaptopropanoic acid. Substitution of 6-bromo derivative of progesterone using the same reagent unexpectedly afforded a C-4 substituted product instead of the normal C-6 substituted product previously reported in the literature.
Yoshida
H
H
Department of Organo-chemical Research, Rohto Pharmaceutical Co., Ltd., Osaka, Japan.
Nakai
S
S
Nimbari
F
F
Yoshimoto
K
K
Nishimura
T
T
D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D006241:Haptens; D006908:Hydroxyprogesterones / Q000276:immunology*; D008279:Magnetic Resonance Imaging; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared
D006241:Haptens; D006908:Hydroxyprogesterones; C030228:11-hydroxyprogesterone