title: Synthesis of 11 alpha-hydroxyprogesterone haptens.
abstract: 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.
authors.affiliation: Department of Organo-chemical Research, Rohto Pharmaceutical Co., Ltd., Osaka, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Yoshida
authors.forename: S
authors.initials: S
authors.lastname: Nakai
authors.forename: F
authors.initials: F
authors.lastname: Nimbari
authors.forename: K
authors.initials: K
authors.lastname: Yoshimoto
authors.forename: T
authors.initials: T
authors.lastname: Nishimura
mesh_terms: 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
chemical_list: D006241:Haptens; D006908:Hydroxyprogesterones; C030228:11-hydroxyprogesterone