0387886 - ÚMG 2013 RIV DE eng J - Journal Article
Hessler, F. - Císařová, I. - Sedlák, David - Bartůněk, Petr - Kotora, Martin
Synthesis of ferrocenestrone: the first metallocene based steroid analogue.
Chemistry - A European Journal. Roč. 18, č. 18 (2012), s. 5515-5518. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA MŠMT(CZ) 1M0508; GA ČR GA204/09/1905; GA MŠMT(CZ) LC06077
Institutional support: RVO:68378050 ; RVO:61388963
Keywords : asymmetric synthesis * ferrocenestrones * metallocenes * steroids * synthesis design
Subject RIV: EB - Genetics ; Molecular Biology
Impact factor: 5.831, year: 2012

Ferrocenestrone, the first steroid derivative containing a metallocene moiety, was stereoselectively prepared (see scheme). 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.
Permanent Link: http://hdl.handle.net/11104/0218363