title: Diacetoxyiodobenzene-mediated synthesis of unnatural furospirostane sapogenins derived from diosgenin and tigogenin.
abstract: Two unnatural steroid sapogenins bearing a furospirostane side chain were prepared starting from the readily available spirostane sapogenins, tigogenin and diosgenin following a synthetic protocol that included: (i) introduction of a carbonyl group at position C-23, (ii) diacetoxyiodobenzene-induced F-ring contraction and (iii) LiAlH4 reduction of the newly emerged methoxycarbonyl moiety. The structures of the new compounds were corroborated by NMR and X-ray studies.
authors.affiliation: Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México D.F., Mexico.
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Sánchez-Flores
authors.forename: Margarita
authors.initials: M
authors.lastname: Romero-Ávila
authors.forename: Anielka
authors.initials: A
authors.lastname: Rosado-Abón
authors.forename: Marcos
authors.initials: M
authors.lastname: Flores-Álamo
authors.forename: Martín A
authors.initials: MA
authors.lastname: Iglesias-Arteaga
mesh_terms: D000085:Acetates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004144:Diosgenin / Q000737:chemistry*; D006868:Hydrolysis; D007462:Iodobenzenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D012502:Sapogenins / Q000138:chemical synthesis*; D013150:Spirostans / Q000737:chemistry*
chemical_list: D000085:Acetates; D007462:Iodobenzenes; D012502:Sapogenins; D013150:Spirostans; C046297:sarsasapogenin; D004144:Diosgenin
keywords: Furospirostane NMR; Furospirostane synthesis; Organic hypervalent iodine compounds; X-ray