An expedient synthesis of the fibril binding compound FSB via sequential Pd-catalyzed coupling reactions.
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%.
Mantel
Mette Louise H
ML
The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
Søbjerg
Lina S
LS
Huynh
Tri H V
TH
Ebran
Jean-Philippe
JP
Lindhardt
Anders T
AT
Nielsen
Niels C
NC
Skrydstrup
Troels
T
D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry
C496440:(E,E)-1-fluoro-2,5-bis-(3-hydroxycarbonyl-4-hydroxy)styrylbenzene; D013343:Styrenes; D010165:Palladium