An expedient synthesis of the fibril binding compound FSB via sequential Pd-catalyzed coupling reactions

Mette Louise H Mantel; Lina S Søbjerg; Tri H V Huynh; Jean-Philippe Ebran; Anders T Lindhardt; Niels C Nielsen; Troels Skrydstrup

doi:10.1021/jo7026189

An expedient synthesis of the fibril binding compound FSB via sequential Pd-catalyzed coupling reactions

J Org Chem. 2008 May 2;73(9):3570-3. doi: 10.1021/jo7026189. Epub 2008 Mar 26.

Authors

Mette Louise H Mantel¹, Lina S Søbjerg, Tri H V Huynh, Jean-Philippe Ebran, Anders T Lindhardt, Niels C Nielsen, Troels Skrydstrup

Affiliation

¹ The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.

PMID: 18363363
DOI: 10.1021/jo7026189

Abstract

The styryl benzene derivative (E, E)-1-fluoro-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene (FSB), well-known for its binding to beta-amyloid peptide fibrils, was synthesized in an efficient manner exploiting two sequential palladium(0)-catalyzed coupling reactions in a 34% overall yield. This is a substantial improvement to the previously reported synthesis of FSB in 1.1%.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Molecular Structure
Palladium / chemistry*
Styrenes / chemical synthesis*
Styrenes / chemistry

Substances

(E,E)-1-fluoro-2,5-bis-(3-hydroxycarbonyl-4-hydroxy)styrylbenzene
Styrenes
Palladium