Stereoselective synthesis and hormonal activity of novel dafachronic acids and naturally occurring steroids isolated from corals

• Main Authors: Saini, Ratni, Boland, Sebastian, Kataeva, Olga, Schmidt, Arndt W., Kurzchalia, Teymuras V., Knölker, Hans-Joachim
• Other Authors: Royal Society of Chemistry,
• Format: Article
• Language: English
• Published: Saechsische Landesbibliothek- Staats- und Universitaetsbibliothek Dresden 2014
• Subjects: Caenorhabditis elegans; Fadenwurm; Kernrezeptor; Lebensdauer; Stereoselektive Synthese; caenorhabditis elegans; nuclear receptor; life span; stereocontrolled synthesis; dauer formation; daf-12; ligands; identification; ergosterol; ddc:540; rvk:VA 1120
• Online Access: http://nbn-resolving.de/urn:nbn:de:bsz:14-qucosa-139217; http://nbn-resolving.de/urn:nbn:de:bsz:14-qucosa-139217; http://www.qucosa.de/fileadmin/data/qucosa/documents/13921/10.1039c2ob25394a.pdf

A stereoselective synthesis of (25S)-Δ1-, (25S)-Δ1,4-, (25S)-Δ1,7-, (25S)-Δ8(14)-, (25S)-Δ4,6,8(14)-dafachronic acid, methyl (25S)-Δ1,4-dafachronate and (25S)-5α-hydroxy-3,6-dioxocholest-7-en-26-oic acid is described. (25S)-Δ1,4-Dafachronic acid and its methyl ester are natural products isolated from corals and have been obtained by synthesis for the first time. (25S)-5α-Hydroxy-3,6-dioxocholest-7-en-26-oic acid represents a promising synthetic precursor for cytotoxic marine steroids. === Dieser Beitrag ist mit Zustimmung des Rechteinhabers aufgrund einer (DFG-geförderten) Allianz- bzw. Nationallizenz frei zugänglich.