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Total Synthesis of Amphidinolide K, a Macrolide That Stabilizes F-Actin
Dani Sánchez1, Thanos Andreou1, Anna M Costa1
1Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona , Av Diagonal 645, 08028 Barcelona, Catalonia, Spain.
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.
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