Issue 11, 2009
From the journal:

Organic & Biomolecular Chemistry

4α-Bromo-5α-cholestan-3β-ol and nor-5α-cholestan-3β-ol derivatives—stereoselective synthesis and hormonal activity in Caenorhabditis elegans†

René Martin,a   Ratni Saini,a   Ingmar Bauer,a   Margit Gruner,a   Olga Kataeva,a   Vyacheslav Zagoriy,b   Eugeni V. Entchev,b   Teymuras V. Kurzchaliab  and  Hans-Joachim Knölker*a  

* Corresponding authors

a Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany
E-mail: hans-joachim.knoelker@tu-dresden.de
Fax: +49 351-463-37030

b Max Planck Institute of Molecular Cell Biology and Genetics, Pfotenhauerstrasse 108, 01307 Dresden, Germany

Abstract

We describe the stereoselective synthesis of 4α-bromo-5α-cholestan-3β-ol, 21-nor-5α-cholestan-3β-ol, 27-nor-5α-cholestan-3β-ol and 21,27-bisnor-5α-cholestan-3β-ol. In order to clarify the in vivometabolism 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.

Graphical abstract: 4α-Bromo-5α-cholestan-3β-ol and nor-5α-cholestan-3β-ol derivatives—stereoselective synthesis and hormonal activity in Caenorhabditis elegans

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Article information

DOI
https://doi.org/10.1039/B904001C
Article type
Paper
Submitted
26 Feb 2009
Accepted
17 Mar 2009
First published
16 Apr 2009

Org. Biomol. Chem., 2009,7, 2303-2309

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4α-Bromo-5α-cholestan-3β-ol and nor-5α-cholestan-3β-ol derivatives—stereoselective synthesis and hormonal activity in Caenorhabditis elegans

R. Martin, R. Saini, I. Bauer, M. Gruner, O. Kataeva, V. Zagoriy, E. V. Entchev, T. V. Kurzchalia and H. Knölker, Org. Biomol. Chem., 2009, 7, 2303 DOI: 10.1039/B904001C

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