title: An improved route to (+)-tedanolide and analysis of its subtle effects controlling conformation and biological behaviour.
abstract: The improved synthesis of the antitumor compound (+)-tedanolide is described through an aldol coupling of bis-ketone 7. This modification shortens the synthetic steps in the endgame and provides rapid access to this biologically important natural product. Additionally, it serves as a probe in order to unravel the conformational effects that impede or enable its successful synthesis. Having this way access to des-epoxy-tedanolide, its biological characterization surprisingly unravelled the mode of action to resemble candidaspongiolide rather than deoxytedanolide.
authors.affiliation: Leibniz Universität Hannover, Institut für Organische Chemie, Schneiderberg 1B, 30167 Hannover, Germany.
authors.forename: Nina
authors.initials: N
authors.lastname: Diaz
authors.forename: Mingzhao
authors.initials: M
authors.lastname: Zhu
authors.forename: Gunnar
authors.initials: G
authors.lastname: Ehrlich
authors.forename: Ulrike
authors.initials: U
authors.lastname: Eggert
authors.forename: Yazh
authors.initials: Y
authors.lastname: Muthukumar
authors.forename: Florenz
authors.initials: F
authors.lastname: Sasse
authors.forename: Markus
authors.initials: M
authors.lastname: Kalesse
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D002460:Cell Line; D006801:Humans; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C409106:13-deoxytedanolide; D000970:Antineoplastic Agents; D001688:Biological Products; D018942:Macrolides; C531429:candidaspongiolide; C119775:tedanolide