Library of biphenyl privileged substructures using a safety-catch linker approach.
A biphenyl privileged structure library containing three attachment points were synthesized using a catechol-based safety-catch linker strategy. The method requires the attachment of a bromo-acid to the linker, followed by a Pd-catalyzed Suzuki cross-coupling reaction. Further derivatization, activation of the linker with strong acid and aminolysis afforded the respective products in high purity and good overall yield. To show the versatility of the synthesis, a 199-member library was generated. The library samples both conformational and chemical diversity about a well-known privileged substructure.
Severinsen
Rune
R
Institute for Molecular Bioscience, The University of Queensland, St. Lucia, 4072 Queensland, Australia.
Bourne
Gregory T
GT
Tran
Tran T
TT
Ankersen
Michael
M
Begtrup
Mikael
M
Smythe
Mark L
ML
D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D015394:Molecular Structure
D001713:Biphenyl Compounds; D003432:Cross-Linking Reagents; C010574:biphenyl