Balssa Frédéric, Fischer Michael, Bonnaire Yves
Laboratoire des Courses Hippiques, 15 rue de Paradis, 91370 Verrières le Buisson, France.
Laboratoire des Courses Hippiques, 15 rue de Paradis, 91370 Verrières le Buisson, France.
Steroids. 2014 Aug;86:1-4. doi: 10.1016/j.steroids.2014.04.009. Epub 2014 May 1.
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.
