title: C-H Acetoxylation-Based Chemical Synthesis of 17 β-Hydroxymethyl-17 α-methyl-18-norandrost-13-ene Steroids.
abstract: Palladium-catalyzed C-H acetoxylation has been proposed as a key transformation in the first chemical synthesis of steroids bearing a unique 17β-hydroxymethyl-17α-methyl-18-nor-13-ene D-fragment. This C-H functionalization step was crucial for inverting the configuration at the quaternary stereocenter of a readily available synthetic intermediate. The developed approach was applied to prepare the metandienone metabolite needed as a reference substance in anti-doping analysis to control the abuse of this androgenic anabolic steroid.
authors.affiliation: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141, Minsk, Belarus. ahurski@iboch.bas-net.by.
authors.forename: Alaksiej L
authors.identifier: http://orcid.org/0000-0002-8599-2621
authors.initials: AL
authors.lastname: Hurski
authors.affiliation: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141, Minsk, Belarus.
authors.forename: Maryia V
authors.identifier: http://orcid.org/0000-0001-6443-1940
authors.initials: MV
authors.lastname: Barysevich
authors.affiliation: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141, Minsk, Belarus.
authors.forename: Tatsiana S
authors.identifier: http://orcid.org/0000-0003-2112-542X
authors.initials: TS
authors.lastname: Dalidovich
authors.affiliation: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141, Minsk, Belarus.
authors.forename: Marharyta V
authors.identifier: http://orcid.org/0000-0001-9267-0113
authors.initials: MV
authors.lastname: Iskryk
authors.affiliation: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141, Minsk, Belarus.
authors.forename: Nastassia U
authors.identifier: http://orcid.org/0000-0003-3468-7544
authors.initials: NU
authors.lastname: Kolasava
authors.affiliation: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141, Minsk, Belarus.
authors.forename: Vladimir N
authors.identifier: http://orcid.org/0000-0001-8591-2794
authors.initials: VN
authors.lastname: Zhabinskii
authors.affiliation: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141, Minsk, Belarus.
authors.forename: Vladimir A
authors.identifier: http://orcid.org/0000-0002-3850-9860
authors.initials: VA
authors.lastname: Khripach
mesh_terms: D045930:Anabolic Agents / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D008696:Methandrostenolone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009635:Norandrostanes / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000626190:17beta-hydroxymethyl-17alpha-methyl-18-norandrost-13-ene; D045930:Anabolic Agents; D009635:Norandrostanes; D010165:Palladium; D008696:Methandrostenolone
keywords: C−H activation; oxidation; protecting groups; rearrangement; steroids