Synthesis of Ferrocenestrone: the First Metallocene Based Steroid Analogue

Abstract

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.

Keywords

• asymmetric synthesis
• ferrocenestrones
• metallocenes
• steroids
• synthesis design