title: Lewis Acid Mediated Nazarov Cyclization as a Convergent and Enantioselective Entry to C-nor-D-homo-Steroids.
abstract: A straightforward synthesis of C-nor-D-homo steroids starting from (+)-Wieland-Miescher ketone is reported. This convergent synthetic strategy utilizes a scalable diastereoselective Nazarov cyclization of functionalized chiral aryl vinyl ketones, allowing for further functionalization. The ability to conduct this key transformation on a multi-gram scale paves the way for the synthesis of a variety of completely new C-nor-D-homo steroids, without the need of a classic steran steroid rearrangement or achiral linear reaction sequences.
authors.affiliation: Institut für Organische Chemie, Fakultät für Chemie und Mineralogie, Universität Leipzig, Johannisallee 29, 04103, Leipzig, Germany.
authors.forename: Johannes
authors.identifier: http://orcid.org/0000-0002-8905-3816
authors.initials: J
authors.lastname: Krieger
authors.affiliation: Institut für Organische Chemie, Fakultät für Chemie und Mineralogie, Universität Leipzig, Johannisallee 29, 04103, Leipzig, Germany.
authors.forename: Toni
authors.initials: T
authors.lastname: Smeilus
authors.affiliation: Institut für Organische Chemie, Fakultät für Chemie und Mineralogie, Universität Leipzig, Johannisallee 29, 04103, Leipzig, Germany.
authors.forename: Oliver
authors.initials: O
authors.lastname: Schackow
authors.affiliation: Institut für Organische Chemie, Fakultät für Chemie und Mineralogie, Universität Leipzig, Johannisallee 29, 04103, Leipzig, Germany.
authors.forename: Athanassios
authors.identifier: http://orcid.org/0000-0003-2203-0959
authors.initials: A
authors.lastname: Giannis
keywords: Lewis acids; electrocyclic reactions; natural products; steroids; umpolung