Stereoselective synthesis of the hormonally active (25S)-Δ7-dafachronic acid, (25S)-Δ4-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid

René Martin; Frank Däbritz; Eugeni V. Entchev; Teymuras V. Kurzchalia; Hans-Joachim Knölker

doi:10.1039/B815064H

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Stereoselective synthesis of the hormonally active (25S)-Δ⁷-dafachronic acid, (25S)-Δ⁴-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid†

René Martin,^a Frank Däbritz,^a Eugeni V. Entchev,^b Teymuras V. Kurzchalia^b and Hans-Joachim Knölker*^a

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* Corresponding authors

^a Department Chemie, Technische Universität Dresden, Bergstrasse 66, Germany
E-mail: hans-joachim.knoelker@tu-dresden.de
Fax: +49 35-463-37030

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

Abstract

We report a stereoselective synthesis of the (25S)-cholestenoic-26-acids which are highly efficient ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans.

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Article information

DOI: https://doi.org/10.1039/B815064H
Article type: Communication
Submitted: 29 Aug 2008
Accepted: 02 Oct 2008
First published: 17 Oct 2008

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Org. Biomol. Chem., 2008,6, 4293-4295

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Stereoselective synthesis of the hormonally active (25S)-Δ⁷-dafachronic acid, (25S)-Δ⁴-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid

R. Martin, F. Däbritz, E. V. Entchev, T. V. Kurzchalia and H. Knölker, Org. Biomol. Chem., 2008, 6, 4293 DOI: 10.1039/B815064H

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Organic & Biomolecular Chemistry