title: Stereoselective synthesis and hormonal activity of novel dafachronic acids and naturally occurring steroids isolated from corals.
abstract: A stereoselective synthesis of (25S)-Δ(1)-, (25S)-Δ(1,4)-, (25S)-Δ(1,7)-, (25S)-Δ(8(14))-, (25S)-Δ(4,6,8(14))-dafachronic acid, methyl (25S)-Δ(1,4)-dafachronate and (25S)-5α-hydroxy-3,6-dioxocholest-7-en-26-oic acid is described. (25S)-Δ(1,4)-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.
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
authors.forename: Ratni
authors.initials: R
authors.lastname: Saini
authors.forename: Sebastian
authors.initials: S
authors.lastname: Boland
authors.forename: Olga
authors.initials: O
authors.lastname: Kataeva
authors.forename: Arndt W
authors.initials: AW
authors.lastname: Schmidt
authors.forename: Teymuras V
authors.initials: TV
authors.lastname: Kurzchalia
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Knölker
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D017173:Caenorhabditis elegans / Q000187:drug effects* / Q000235:genetics / Q000254:growth & development; D029742:Caenorhabditis elegans Proteins / Q000235:genetics; D002782:Cholestenes / Q000138:chemical synthesis* / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D004952:Esters / Q000138:chemical synthesis / Q000494:pharmacology; D007814:Larva / Q000187:drug effects / Q000235:genetics / Q000254:growth & development; D015394:Molecular Structure; D018160:Receptors, Cytoplasmic and Nuclear / Q000172:deficiency / Q000235:genetics; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D029742:Caenorhabditis elegans Proteins; D002782:Cholestenes; C410905:DAF-12 protein, C elegans; D004952:Esters; D018160:Receptors, Cytoplasmic and Nuclear; C533800:dafachronic acid