Synthesis of 13,14-secotestosterone derivatives

Хрипач, В. А.; Жабинский, В. Н.; Kuchto, Anna I.; Zhiburtovich, Yuliya Y.; Fando, Galina P.; Lyakhov, Alexander S.; Govorova, A. A.; Groen, Marinus B.; Louw, Jaap van der; Groot, Aede de

doi:10.1016/j.steroids.2004.04.010

Cited by 9 publications

(3 citation statements)

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“…10 This approach was successfully used to prepare a number of androstane 13,14-seco steroids. 11,12 The main idea of the present investigation, which aimed to develop new synthetic approaches to 5,10-seco steroids, was to examine the influence of a carbonyl group at C-1 (in β-position to hydroxyl group at C-5) on the course of radical oxidation.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and radical oxidation of steroidal 1-oxo-5α-alcohols

Хрипач¹,

Жабинский²,

Fando³

et al. 2008

Arkivoc

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A new synthetic approach is described for the preparation of steroidal 1-oxo-5α-alcohols. A key step in the synthesis was the [2,3]sigmatropic rearrangement of allylic 3α-selenide ensuring the introduction of the desired functional groups at C-1 and C-5. The radical oxidation of 1-oxo-5α-alcohol was shown to proceed with the formation of 5,10-seco steroid. Its structural assignment was based on NMR and CD spectroscopic studies.

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Section: Methodsmentioning

confidence: 99%

Synthesis and radical oxidation of steroidal 1-oxo-5α-alcohols

Хрипач¹,

Жабинский²,

Fando³

et al. 2008

Arkivoc

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“…Further work has been reported on the preparation of 13,14seco-steroids by the Grob fragmentation of 14a-hydroxy-17btosyloxy steroids, 21 → 22, 48 and by the lead tetra-acetate and iodine oxidation of 14a-hydroxy-17-keto steroids. 49 The reaction of (13S)-13-iodo-16b-methoxy-3a,5a-cyclo-13,14-secoandrostan-14,17-dione with hydroxylamine has been examined. 50 A simple synthesis of gestodene 23 from 18-methylestr-4-ene-3,17-dione has been reported.…”

Section: Androstanesmentioning

confidence: 99%

“…49 The reaction of (13S)-13-iodo-16b-methoxy-3a,5a-cyclo-13,14-secoandrostan-14,17-dione with hydroxylamine has been examined. 50 A simple synthesis of gestodene 23 from 18-methylestr-4-ene-3,17-dione has been reported. 51 The detection of 17-alkyl substituted anabolic steroids by liquid chromatography and electrospray tandem mass spectrometry has been examined in relation to the abuse of these steroids.…”

Section: Androstanesmentioning

confidence: 99%

Steroids: partial synthesis in medicinal chemistry

Hanson

2006

Nat. Prod. Rep.

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Designer Steroids

Kazlauskas

2009

Handbook of Experimental Pharmacology

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Anabolic steroids have been studied for over 50 years and during that time numerous compounds with a variety of functional groups have been produced and many have been published. Of these only a small number have been introduced to the pharmaceutical market. WADA has continued the work begun by the IOC banning the use of these agents within sport as performance enhancing substances. Athletes, however, continue to use these anabolic steroids but tighter testing and the introduction of unannounced sample collection has made this form of cheating harder.In order to try to evade detection, athletes who continue to dope are having to resort to the use of a far more dangerous form of drug - the designer steroid. These steroids are manufactured to closely resemble existing known compounds, but with sufficient chemical diversity to ensure that their detection by the WADA accredited laboratories is more difficult. A worrying feature of the use of these compounds is that no data is available to evaluate either the efficacy or the safety of these substances. Many such drugs are now being made in clandestine ways (as demonstrated by the recent BALCO case) and then passed on to athletes who become the guinea pigs determining the potential of the substances as doping agents.Methods for the detection of these new compounds are being developed using emerging techniques such as gas chromatography or liquid chromatography attached to a variety of mass spectrometry instruments. This technology as well as vigilance by laboratories and enforcement agencies can all help in early detection of designer steroids being used for doping.

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Synthesis of 13,14-secotestosterone derivatives

Cited by 9 publications

References 20 publications

Synthesis and radical oxidation of steroidal 1-oxo-5α-alcohols

Synthesis and radical oxidation of steroidal 1-oxo-5α-alcohols

Steroids: partial synthesis in medicinal chemistry

Designer Steroids

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