Synthesis and biological activity of the (25R)-cholesten-26-oic acids—ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans†,10.1039/B817358C

热搜：

Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

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

René Martin,Arndt W. Schmidt,Gabriele Theumer,Tilo Krause,Eugeni V. Entchev,Teymuras V. Kurzchalia,Hans-Joachim Knölker

Organic & Biomolecular Chemistry Pub Date : 01/27/2009 00:00:00 , DOI:10.1039/B817358C

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.