title: Thermodynamic Meerwein-Ponndorf-Verley reduction in the diastereoselective synthesis of 17α-estradiol.
abstract: The synthesis of 17α-hydroxy steroids generally requires multiple synthetic manipulations. The synthesis of 17α-estradiol is no exception, as this process involves the protection and release of the 3-hydroxy functional group. The diastereoselective reduction of the 17-keto-steroid can be utilized to prepare 17α-hydroxy-steroids. Here, 17α-estradiol was synthesized from commercially available estrone under thermodynamic Meerwein-Ponndorf-Verley (MPV) conditions in a single step, followed by simple chromatographic separation over silica gel. The remaining mixture of unreacted estrone and estradiols was easily recycled through Oppenauer oxidation to estrone, with an overall yield of 68% 17α-estradiol.
authors.affiliation: Evestra, Inc., San Antonio, TX, USA. Electronic address: gahmed@evestra.com.
authors.forename: Gulzar
authors.initials: G
authors.lastname: Ahmed
authors.affiliation: Evestra, Inc., San Antonio, TX, USA.
authors.forename: Klaus
authors.initials: K
authors.lastname: Nickisch
mesh_terms: D004958:Estradiol / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry; D013816:Thermodynamics
chemical_list: D013256:Steroids; D004958:Estradiol
keywords: Estradiol-α; Meerwein-Ponndorf-Verley reduction; Steroid