Issue 5, 2009
From the journal:

Organic & Biomolecular Chemistry

Synthesis and biological activity of the (25R)-cholesten-26-oic acids—ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans†

René Martin,a   Arndt W. Schmidt,a   Gabriele Theumer,a   Tilo Krause,a   Eugeni V. Entchev,b   Teymuras V. Kurzchaliab  and  Hans-Joachim Knölker*a  

* Corresponding authors

a Department Chemie, Technische Universität Dresden, Bergstrasse 66, 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, Germany

Abstract

We describe the stereoselective transformation of diosgenin (4a) to (25R)-Δ4-dafachronic acid (1a), (25R)-Δ7-dafachronic acid (2a), and (25R)-cholestenoic acid (3a), which represent potential ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans. Key-steps of our synthetic approach are a modified Clemmensen reduction of diosgenin (4a) and a double bond shift from the 5,6- to the 7,8-position. In the 25R-series, the Δ7-dafachronic acid 2a exhibits the highest hormonal activity.

Graphical abstract: Synthesis and biological activity of the (25R)-cholesten-26-oic acids—ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans

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Article information

DOI
https://doi.org/10.1039/B817358C
Article type
Paper
Submitted
06 Oct 2008
Accepted
27 Nov 2008
First published
27 Jan 2009

Org. Biomol. Chem., 2009,7, 909-920

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Synthesis and biological activity of the (25R)-cholesten-26-oic acids—ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans

R. Martin, A. W. Schmidt, G. Theumer, T. Krause, E. V. Entchev, T. V. Kurzchalia and H. Knölker, Org. Biomol. Chem., 2009, 7, 909 DOI: 10.1039/B817358C

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