Total Synthesis of Amphidinolide K, a Macrolide That Stabilizes F-Actin
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- 作者：Dani S谩nchez ; Thanos Andreou ; Anna M. Costa ; Kevin G. Meyer ; David R. Williams ; Isabel Barasoain ; J. Fernando D铆az ; Daniel Lucena-Agell ; Jaume Vilarrasa
- 刊名：Journal of Organic Chemistry
- 出版年：2015
- 出版时间：September 4, 2015
- 年：2015
- 卷：80
- 期：17
- 页码：8511-8519
- 全文大小：476K
- ISSN：1520-6904
文摘
The total synthesis of (鈭?-amphidinolide K (1) based on asymmetric addition of allylsilane C1鈥?b>C8 to enal C9鈥?b>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 伪,尾-tubulin鈥搈icrotubule and/or G-actin鈥揊-actin equilibria. Compound 1 behaves as a stabilizer of actin filaments (F-actin) in vitro.