Synthesis of 5,10-seco analogs of testosterone.
A number of 5,10-seco analogs of testosterone has been synthesized starting from products of the radical oxidation of 3beta,17beta-diacetoxy-5alpha-androstan-5alpha-ol. The obtained compounds possess a flexible 10-membered ring with substituents (O, -OH) at C-3 and C-5. Similar derivatives with an (E)- and (Z)-Delta(1(10))-double bond have been prepared also. X-ray analysis and a combination of NMR experiments have been used for their structure elucidation and conformation analysis.
Khripach
Vladimir A
VA
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk, Belarus. khripach@iboch.ba-net.by
Zhabinskii
Vladimir N
VN
Kuchto
Anna I
AI
Zhiburtovich
Yuliya Y
YY
Khripach
Natalya B
NB
Lyakhov
Alexander S
AS
Groen
Marinus B
MB
van der Louw
Jaap
J
de Groot
Aede
A
D003460:Crystallization; D018360:Crystallography, X-Ray; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D012632:Secosteroids / Q000138:chemical synthesis*; D013739:Testosterone / Q000031:analogs & derivatives / Q000138:chemical synthesis*
D012632:Secosteroids; D013739:Testosterone