title: Synthesis of novel 13α-18-nor-16-carboxamido steroids via a palladium-catalyzed aminocarbonylation reaction.
abstract: 13α-18-nor-16-Carboxamido steroids were synthesized via a palladium-catalyzed aminocarbonylation reaction of the corresponding iodoalkenes. The starting material was an unnatural 13α-16-keto steroid, obtained by a Wagner-Meerwein rearrangement of a 16α,17α-epoxide in the presence of [BMIM][BF4]. The 13α-16-keto steroid was converted to a mixture of 16-iodo-16-ene and 16-iodo-15-ene derivatives in two steps by Barton's methodology. Aminocarbonylation of the steroidal alkenyl iodides was carried out using different primary and secondary amines as nucleophiles. The products, 16-carboxamido-16-ene and 16-carboxamido-15-ene derivatives, were obtained in good yields and were characterized by (1)H and (13)C NMR, IR and MS. The reduction of the above two unsaturated carboxamides resulted in the same product, 17α-methyl-16α-carboxamido-androstane.
authors.affiliation: University of Pannonia, Institute of Chemistry, Department of Organic Chemistry, Egyetem u. 10, P.O. Box 158, H-8200 Veszprém, Hungary.
authors.forename: Eszter
authors.initials: E
authors.lastname: Szánti-Pintér
authors.forename: Zsolt
authors.initials: Z
authors.lastname: Csók
authors.forename: Zoltán
authors.initials: Z
authors.lastname: Berente
authors.forename: László
authors.initials: L
authors.lastname: Kollár
authors.forename: Rita
authors.initials: R
authors.lastname: Skoda-Földes
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000731:Androstanes / Q000138:chemical synthesis*; D002384:Catalysis; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D009025:Morpholines / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D010165:Palladium / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000731:Androstanes; D006847:Hydrocarbons, Iodinated; D009025:Morpholines; D010165:Palladium; C037574:morpholine
keywords: 13α-18-nor-Steroid; Aminocarbonylation; Iodoalkene; Palladium