Synthesis of Fmoc-Protected Arylphenylalanines (Bip Derivatives) via Nonaqueous Suzuki-Miyaura Cross-Coupling Reactions.
A one-step synthesis of Fmoc-protected aryl/heteroaryl-substituted phenylalanines (Bip derivatives) using the nonaqueous palladium-catalyzed Suzuki-Miyaura cross-coupling (SMC) reaction of Fmoc-protected bromo- or iodophenylalanines is reported. This protocol allows for the direct formation of a variety of unnatural biaryl-containing amino acids in good to excellent yield, which can be readily used in subsequent Fmoc solid-phase peptide synthesis. The synthetic utility of this method is also demonstrated by the SMC reaction of bromophenylalanine-containing tripeptides.
Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
Jennifer X
JX
Qiao
Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
Kenneth J
KJ
Fraunhoffer
Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
Yi
Y
Hsiao
Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
Yi-Xin
YX
Li
Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
Chunlei
C
Wang
Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
Tammy C
TC
Wang
Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
Michael A
MA
Poss