title: An easy stereoselective synthesis of 5(10)-estrene-3β,17α-diol, a biological marker of pregnancy in the mare.
abstract: 5(10)-Estrene-3β,17α-diol is an essential reference material for doping analysis in horse-racing laboratories. It is used to detect misuse, for doping purpose, of the pregnancy status in the mare. Its stereoselective synthesis from 17β-estradiol-3-methyl ether (prepared from estrone or 17β-estradiol) was performed in four steps: (1) Mitsunobu inversion of the 17β-alcohol; (2) Birch reduction of the aromatic ring; (3) stereoselective reduction of the 3-ketone via Noyori asymmetric transfer hydrogenation; (4) chemoenzymatic purification.
authors.affiliation: Laboratoire des Courses Hippiques, 15 rue de Paradis, 91370 Verrières le Buisson, France. Electronic address: f.balssa@lchfrance.fr.
authors.forename: Frédéric
authors.initials: F
authors.lastname: Balssa
authors.affiliation: Laboratoire des Courses Hippiques, 15 rue de Paradis, 91370 Verrières le Buisson, France.
authors.forename: Michael
authors.initials: M
authors.lastname: Fischer
authors.affiliation: Laboratoire des Courses Hippiques, 15 rue de Paradis, 91370 Verrières le Buisson, France.
authors.forename: Yves
authors.initials: Y
authors.lastname: Bonnaire
mesh_terms: D000818:Animals; D015415:Biomarkers / Q000378:metabolism; D004963:Estrenes / Q000138:chemical synthesis* / Q000737:chemistry; D005260:Female; D006736:Horses / Q000378:metabolism*; D008968:Molecular Conformation; D011247:Pregnancy; D011270:Pregnancy, Animal / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D015415:Biomarkers; D004963:Estrenes; C041287:3,17-dihydroxy-5-estrene
keywords: 5(10)-Estrene-3β,17α-diol; Chemoenzymatic; Doping; Horse; Noyori hydrogenation; Pregnancy