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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

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Entchev,  Eugeni V
Max Planck Institute of Molecular Cell Biology and Genetics, Max Planck Society;

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Kurzchalia,  Teymuras V
Max Planck Institute of Molecular Cell Biology and Genetics, Max Planck Society;

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Citation

Martin, R., Schmidt, A. W., Theumer, G., Krause, T., Entchev, E. V., Kurzchalia, T. V., et al. (2009). Synthesis and biological activity of the (25R)-cholesten-26-oic acids-ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans. Organic & Biomolecular Chemistry, 7(5), 909-920.


Cite as: https://hdl.handle.net/21.11116/0000-0001-0D82-E
Abstract
We describe the stereoselective transformation of diosgenin () to (25R)-Delta(4)-dafachronic acid (), (25R)-Delta(7)-dafachronic acid (), and (25R)-cholestenoic acid (), 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 () and a double bond shift from the 5,6- to the 7,8-position. In the 25R-series, the Delta(7)-dafachronic acid exhibits the highest hormonal activity.