title: The plakotenins: biomimetic Diels-Alder reactions, total synthesis, structural investigations, and chemical biology.
abstract: The total synthesis of plakotenin, a cytotoxic marine natural product, using a biomimetic Diels-Alder reaction is described in detail. Two approaches were used, whereby the Diels-Alder reaction occurs at different stages of the synthesis. Homo- and nor-plakotenin, related natural products, were also prepared, as well as iso-plakotenin, a diastereoisomer of plakotenin. The syntheses prove the relative and absolute stereochemistry of the latter. The chemical biology of the plakotenins was investigated on selected compounds.
authors.affiliation: Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Campus South, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Bourcet
authors.forename: Larissa
authors.initials: L
authors.lastname: Kaufmann
authors.forename: Stephanie
authors.initials: S
authors.lastname: Arzt
authors.forename: Angela
authors.initials: A
authors.lastname: Bihlmeier
authors.forename: Wim
authors.initials: W
authors.lastname: Klopper
authors.forename: Ute
authors.initials: U
authors.lastname: Schepers
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D008968:Molecular Conformation; D047229:Plakortis / Q000737:chemistry; D011789:Quantum Theory; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D002264:Carboxylic Acids; C400358:plakotenin