title: Synthesis of 13,14-secotestosterone derivatives.
abstract: A number of testosterone analogs with a 13,14-secosteroidal fragment have been prepared from (13S)-13-iodo-6beta-methoxy-3alpha, 5-cyclo-13,14-seco-5alpha-androstan-14,17-dione. The key steps involved stereoselective deiodination of the starting compound with triphenylphosphine and selective protection of the 17-keto group with trimethylsilylcyanide. Removal of iodine at C-13 proceeded with inversion of the configuration at C-13, which has been established by X-ray crystallography. 13,14-Secotestosterone analogues substituted and non-substituted at C-14 have been prepared. The obtained compounds containing flexible CD ring fragments are of great interest for comparative studies in biological tests together with testosterone and other steroids with a rigid tetracyclic skeleton.
authors.affiliation: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Street 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: Anna I
authors.initials: AI
authors.lastname: Kuchto
authors.forename: Yuliya Y
authors.initials: YY
authors.lastname: Zhiburtovich
authors.forename: Galina P
authors.initials: GP
authors.lastname: Fando
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: D008958:Models, Molecular; D008968:Molecular Conformation; D012632:Secosteroids / Q000138:chemical synthesis*; D013739:Testosterone / Q000031:analogs & derivatives / Q000138:chemical synthesis*
chemical_list: D012632:Secosteroids; D013739:Testosterone