Derivatives of 16alpha-hydroxy-dehydroepiandrosterone with an additional 7-oxo or 7-hydroxy substituent: synthesis and gas chromatography/mass spectrometry analysis.
Derivatives of 16alpha-hydroxy-dehydroepiandrosterone, which have an additional oxygen substituent at position 7 (oxo or hydroxy group), were synthesized. Firstly, 17,17-dimethoxyandrost-5-ene-3beta,16alpha-diyl diacetate was prepared and then oxidized with a complex of chromium(VI) oxide and 2,5-dimethylpyrazole to the respective 7-oxo derivative. This key intermediate was both deprotected or reduced by l-Selectride or sodium borohydride in the presence of cerium(III) chloride and then deprotected to give 7-oxo, 7alpha-hydroxy and 7beta-hydroxy derivatives of 16alpha-hydroxy-dehydroepiandrosterone. The target compounds were characterized by (1)H and (13)C NMR spectra and in the form of O-methyloxime-trimethylsilyl derivatives, by gas chromatography/mass spectrometry methods.
Pouzar
Vladimír
V
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic.
Cerný
Ivan
I
Hill
Martin
M
Bicíková
Marie
M
Hampl
Richard
R
D001894:Borohydrides; D002563:Cerium; D002712:Chlorides; D003687:Dehydroepiandrosterone / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006900:Hydroxylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction
D001894:Borohydrides; D002712:Chlorides; D007202:Indicators and Reagents; C011277:16-hydroxydehydroepiandrosterone; D002563:Cerium; D003687:Dehydroepiandrosterone; C025364:sodium borohydride