Steroid total synthesis. 11. (+)-Estr-4-ene-3,17-dione from a chiral lactone

Rosenberger, Michael; Borer, R.; Saucy, G.

doi:10.1021/jo00402a015

Cited by 15 publications

(4 citation statements)

References 3 publications

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“…Chemical shift of d 220.4 for 17-carbonyl group in 13 C-NMR, absence of H-17 signal in 1 H-NMR around d 3.5-4.5, and the occurrence of the molecular ion at m/z 272 indicated oxidation of C-17 in compound III resulting in compound II. These two metabolites were identified as 17b-hydroxyestr-4-en-3-one and estr-4-en-3,17-dione, respectively, and have been previously reported by Hanson and coworkers [14].…”

Section: Resultssupporting

confidence: 76%

Microbial Transformation of Nandrolone Decanoate by Acremonium Strictum

Yazdi¹,

Zanjanian²,

Faramarzi³

et al. 2006

Archiv der Pharmazie

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Estr-4-en-3,17-dione II, 17beta-hydroxyestr-4-en-3-one III, 15alpha-hydroxyestr-4-en-3,17-dione IV, and 15alpha,17beta-dihydroxyestr-4-en-3-one V were produced by microbial transformation of nandrolone decanoate I in the culture of Acremonium strictum PTCC 5282. Bioconversion characteristics observed were ester hydrolysis, oxidation, and hydroxylation. Each microbial product was purified chromatographically and characterized on the basis of spectral data obtained from (1)H-NMR,( 13)C-NMR, FT-IR, MS, and physical constants such as melting point and optical rotation.

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Section: Resultssupporting

confidence: 76%

Microbial Transformation of Nandrolone Decanoate by Acremonium Strictum

Yazdi¹,

Zanjanian²,

Faramarzi³

et al. 2006

Archiv der Pharmazie

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“…Although these data cannot confirm the exact conformation of the steroid detected, this same compound was detected in all these products according to the LC-MS data. [27][28][29] (See supplementary data for the NMR spectra, Figures S31-S34 and S37-S39. )…”

Section: Productmentioning

confidence: 99%

Anabolic steroids detected in bodybuilding dietary supplements – a significant risk to public health

Abbate

Kicman

Evans-Brown

et al. 2014

Drug Testing and Analysis

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Twenty-four products suspected of containing anabolic steroids and sold in fitness equipment shops in the United Kingdom (UK) were analyzed for their qualitative and semi-quantitative content using full scan gas chromatography-mass spectrometry (GC-MS), accurate mass liquid chromatography-mass spectrometry (LC-MS), high pressure liquid chromatography with diode array detection (HPLC-DAD), UV-Vis, and nuclear magnetic resonance (NMR) spectroscopy. In addition, X-ray crystallography enabled the identification of one of the compounds, where reference standard was not available. Of the 24 products tested, 23 contained steroids including known anabolic agents; 16 of these contained steroids that were different to those indicated on the packaging and one product contained no steroid at all. Overall, 13 different steroids were identified; 12 of these are controlled in the UK under the Misuse of Drugs Act 1971. Several of the products contained steroids that may be considered to have considerable pharmacological activity, based on their chemical structures and the amounts present. This could unwittingly expose users to a significant risk to their health, which is of particular concern for naïve users.

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“…It is noteworthy that the small amount of δ-Lactone 1 was hydrolyzed under this condition. With precursor 4 in hand, estra-4,9-diene-3,17-dione was prepared via a domino cyclization approach of compound 4 with an equimolar amount of piperidinium acetate at reflux in toluene 15 , and the final product was obtained in a yield of 32.3%. Attempts to improve the yield of estra-4,9diene-3,17-dione were unsuccessful, the main impurities were less polar and we faild to identified them.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, an convenient construction of this compound would be of great importance. A number of methods have been developed to construct this intermediate in the context of total synthesis [12][13][14][15][16][17][18] . However, these methods often require multiple manipulations, we intended to develop a short and concise synthetic route to estra-4,9-diene-3,17-dione.…”

Section: Introductionmentioning

confidence: 99%