title: Mechanistic insights on the reactivity of furospirostanes with the 16β,22:22,25-diepoxy-23-acetoxymethyl-24-methyl side chain.
abstract: F-ring opening in spirostanes with the 16β,22:22,25-diepoxy-23-acetoxymethyl-24-methyl side chain produces a Δ(22)-intermediate with an allylic acetoxy group. For this reason the reactivity profile of these compounds deviates from that observed in other naturally occurring or synthetic spirostanes and furospirostanes.
authors.affiliation: Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, DF, Mexico.
authors.forename: Mariana
authors.initials: M
authors.lastname: Macías-Alonso
authors.forename: Marcos
authors.initials: M
authors.lastname: Flores-Álamo
authors.forename: Martín A
authors.initials: MA
authors.lastname: Iglesias-Arteaga
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D013150:Spirostans / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004852:Epoxy Compounds; D013150:Spirostans
keywords: Allylic substitution; Bromination; Bromodeacetoxylation; Elimination; Furospirostanes