Total Synthesis of Amphidinolide K, a Macrolide That Stabilizes F-Actin

J Org Chem. 2015 Sep 4;80(17):8511-9. doi: 10.1021/acs.joc.5b00966. Epub 2015 Jun 23.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actins / chemistry*
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Tubulin / chemistry*

Substances

  • Actins
  • Anti-Bacterial Agents
  • Macrolides
  • Tubulin
  • amphidinolide K