Synthesis of 13,14-secotestosterone derivatives.
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.
Khripach
Vladimir A
VA
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Street 5/2, 220141 Minsk. khripach@iboch.bas-net.by
Zhabinskii
Vladimir N
VN
Kuchto
Anna I
AI
Zhiburtovich
Yuliya Y
YY
Fando
Galina P
GP
Lyakhov
Alexander S
AS
Govorova
Alla A
AA
Groen
Marinus B
MB
van der Louw
Jaap
J
de Groot
Aede
A
D008958:Models, Molecular; D008968:Molecular Conformation; D012632:Secosteroids / Q000138:chemical synthesis*; D013739:Testosterone / Q000031:analogs & derivatives / Q000138:chemical synthesis*
D012632:Secosteroids; D013739:Testosterone