title: Total Synthesis of Amphidinolide K, a Macrolide That Stabilizes F-Actin.
abstract: The total synthesis of (-)-amphidinolide K (1) based on asymmetric addition of allylsilane C1-C8 to enal C9-C22 is reported. The 1,9,18-tris-O-TBDPS ether was converted into the desired 9,18-dihydroxy acid. Its macrolactonization was accomplished by the Shiina method. Compound 1 together with some of its stereoisomers and analogues were subjected to evaluation of the possible disruption of the α,β-tubulin-microtubule and/or G-actin-F-actin equilibria. Compound 1 behaves as a stabilizer of actin filaments (F-actin) in vitro.
authors.affiliation: Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona , Av Diagonal 645, 08028 Barcelona, Catalonia, Spain.
authors.forename: Dani
authors.initials: D
authors.lastname: Sánchez
authors.affiliation: Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona , Av Diagonal 645, 08028 Barcelona, Catalonia, Spain.
authors.forename: Thanos
authors.initials: T
authors.lastname: Andreou
authors.affiliation: Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona , Av Diagonal 645, 08028 Barcelona, Catalonia, Spain.
authors.forename: Anna M
authors.initials: AM
authors.lastname: Costa
authors.affiliation: Department of Chemistry, Indiana University , Bloomington, Indiana 47405-7102, United States.
authors.forename: Kevin G
authors.initials: KG
authors.lastname: Meyer
authors.affiliation: Department of Chemistry, Indiana University , Bloomington, Indiana 47405-7102, United States.
authors.forename: David R
authors.initials: DR
authors.lastname: Williams
authors.affiliation: Centro de Investigaciones Biológicas (CIB), CSIC , 28040 Madrid, Spain.
authors.forename: Isabel
authors.initials: I
authors.lastname: Barasoain
authors.affiliation: Centro de Investigaciones Biológicas (CIB), CSIC , 28040 Madrid, Spain.
authors.forename: J Fernando
authors.initials: JF
authors.lastname: Díaz
authors.affiliation: Centro de Investigaciones Biológicas (CIB), CSIC , 28040 Madrid, Spain.
authors.forename: Daniel
authors.initials: D
authors.lastname: Lucena-Agell
authors.affiliation: Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona , Av Diagonal 645, 08028 Barcelona, Catalonia, Spain.
authors.forename: Jaume
authors.initials: J
authors.lastname: Vilarrasa
mesh_terms: D000199:Actins / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014404:Tubulin / Q000737:chemistry*; D000097442:Amphidinolides
chemical_list: D000199:Actins; D000900:Anti-Bacterial Agents; D018942:Macrolides; D014404:Tubulin; C409107:amphidinolide K; D000097442:Amphidinolides