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 3β,17β-diacetoxy-5α-androstan-5α-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)...

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Veröffentlicht in:	Steroids 2008-12, Vol.73 (14), p.1424-1432
Hauptverfasser:	Khripach, Vladimir A., Zhabinskii, Vladimir N., Kuchto, Anna I., Zhiburtovich, Yuliya Y., Khripach, Natalya B., Lyakhov, Alexander S., Groen, Marinus B., van der Louw, Jaap, de Groot, Aede
Format:	Artikel
Sprache:	eng
Schlagworte:	10-membered ring Biological and medical sciences Conformation analysis conformations Crystallization Crystallography, X-Ray Cyclization Fundamental and applied biological sciences. Psychology Magnetic Resonance Spectroscopy medium-sized ring Molecular Conformation radical oxidation reactivity Secosteroids Secosteroids - chemical synthesis steroids Structure elucidation Testosterone Testosterone - analogs & derivatives Testosterone - chemical synthesis Vertebrates: endocrinology X-ray analysis
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Beschreibung
Zusammenfassung:	A number of 5,10-seco analogs of testosterone has been synthesized starting from products of the radical oxidation of 3β,17β-diacetoxy-5α-androstan-5α-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)-Δ 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.
ISSN:	0039-128X 1878-5867
DOI:	10.1016/j.steroids.2008.07.005