title: The synthesis of functionalized 13,14-seco-steroids via Grob fragmentation.
abstract: A synthetic methodology for the synthesis of 13,14-seco-steroids with substituents at C-14 and C-17 is described. The approach involves Grob fragmentation of 14beta-hydroxy-17beta-tosylates, hydroboration-oxidation of the intermediate delta13(17)-olefin, and hydride reduction of the 14-ketone. An unambiguous structural assignment of (13R,14S,17S)-14,17-diacetoxy-3-methoxy-7alpha-methyl-13,14-secoestra-1,3,5(10)-triene was determined by X-ray analysis.
authors.affiliation: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk. khripach@iboch.bas-net.by
authors.forename: Vladimir A
authors.initials: VA
authors.lastname: Khripach
authors.forename: Vladimir N
authors.initials: VN
authors.lastname: Zhabinskii
authors.forename: Galina P
authors.initials: GP
authors.lastname: Fando
authors.forename: Alla I
authors.initials: AI
authors.lastname: Kuchto
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Lyakhov
authors.forename: Alla A
authors.initials: AA
authors.lastname: Govorova
authors.forename: Marinus B
authors.initials: MB
authors.lastname: Groen
authors.forename: Jaap
authors.initials: J
authors.lastname: van der Louw
authors.forename: Aede
authors.initials: A
authors.lastname: de Groot
mesh_terms: D003500:Cyclization; D008958:Models, Molecular; D008968:Molecular Conformation; D012632:Secosteroids / Q000138:chemical synthesis*; D014961:X-Ray Diffraction
chemical_list: D012632:Secosteroids