4Alpha-bromo-5alpha-cholestan-3beta-ol and nor-5alpha-cholestan-3beta-ol derivatives-stereoselective synthesis and hormonal activity in Caenorhabditis elegans

We describe the stereoselective synthesis of 4alpha-bromo-5alpha-cholestan-3beta-ol, 21-nor-5alpha-cholestan-3beta-ol, 27-nor-5alpha-cholestan-3beta-ol and 21,27-bisnor-5alpha-cholestan-3beta-ol. In order to clarify the in vivo metabolism of cholesterol, these compounds have been used for feeding ex...

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Veröffentlicht in:	Organic & biomolecular chemistry 2009-06, Vol.7 (11), p.2303-2309
Hauptverfasser:	Martin, René, Saini, Ratni, Bauer, Ingmar, Gruner, Margit, Kataeva, Olga, Zagoriy, Vyacheslav, Entchev, Eugeni V, Kurzchalia, Teymuras V, Knölker, Hans-Joachim
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Caenorhabditis elegans - metabolism Cholestanols - chemical synthesis Cholestanols - chemistry Cholestanols - metabolism Cholesterol - metabolism Invertebrate Hormones - metabolism Norsteroids - chemical synthesis Norsteroids - chemistry Norsteroids - metabolism Stereoisomerism
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Zusammenfassung:	We describe the stereoselective synthesis of 4alpha-bromo-5alpha-cholestan-3beta-ol, 21-nor-5alpha-cholestan-3beta-ol, 27-nor-5alpha-cholestan-3beta-ol and 21,27-bisnor-5alpha-cholestan-3beta-ol. In order to clarify the in vivo metabolism of cholesterol, these compounds have been used for feeding experiments in Caenorhabditis elegans. Our preliminary results provide important insights into the metabolism of cholesterol in worms.
ISSN:	1477-0539
DOI:	10.1039/b904001c