title: Synthesis of ferrocenestrone: the first metallocene based steroid analogue.
abstract: Ferrocenestrone, the first steroid derivative containing a metallocene moiety, was stereoselectively prepared. The key steps included the enantioselective functionalization of ferrocene, elongation of the side chain, intramolecular enyne metathesis, Diels-Alder reaction, heterogeneous hydrogenation of the sterically hindered double bond, and finally inversion of the configuration at C13.
authors.affiliation: Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Czech Republic.
authors.forename: Filip
authors.initials: F
authors.lastname: Hessler
authors.forename: Ivana
authors.initials: I
authors.lastname: Císařová
authors.forename: David
authors.initials: D
authors.lastname: Sedlák
authors.forename: Petr
authors.initials: P
authors.lastname: Bartůněk
authors.forename: Martin
authors.initials: M
authors.lastname: Kotora
mesh_terms: D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D005296:Ferrous Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006865:Hydrogenation; D000075163:Metallocenes; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D005296:Ferrous Compounds; D000075163:Metallocenes; D009942:Organometallic Compounds; D013256:Steroids; C013108:metallocene; C004998:ferrocene