title: Diels-Alder reaction of androsta-14,16-dien-17-yl acetates with nitroethylene: product distribution and selected adduct transformations.
abstract: The Diels-Alder cycloaddition of nitroethylene to some androsta-14,16-dien-17-yl acetates has been studied. The addition occurs stereoselectively, giving predominantly head-to-head-adduct. 14β-Cyanomethyl steroids were obtained via the reductive cleavage reaction of bridged nitro compounds. The structures of the new compounds have been fully characterized by 2D NMR and tandem mass-spectrometry methods.
authors.affiliation: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Minsk, Belarus. baranovsky@iboch.bas-net.by
authors.forename: Alexander V
authors.initials: AV
authors.lastname: Baranovsky
authors.forename: Dmitry A
authors.initials: DA
authors.lastname: Bolibrukh
authors.forename: Vladimir A
authors.initials: VA
authors.lastname: Khripach
authors.forename: Bernd
authors.initials: B
authors.lastname: Schneider
mesh_terms: D000731:Androstanes / Q000737:chemistry*; D061565:Cycloaddition Reaction; D005030:Ethylenes / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy
chemical_list: D000731:Androstanes; D005030:Ethylenes; D007202:Indicators and Reagents; C036216:ethylene