Tetrahedron

Synthesis of α, α-disubstituted 4-phosphonophenylalanine analogues as conformationally-constrained phosphotyrosyl mimetics

…, H Liu, M Zhang, D Yang, JR Deschamps, TR Burke

Index: Oishi, Shinya; Kang, Sang-Uk; Liu, Hongpeng; Zhang, Manchao; Yang, Dajun; Deschamps, Jeffrey R.; Burke Jr., Terrence R. Tetrahedron, 2004 , vol. 60, # 13 p. 2971 - 2977

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Citation Number: 22

Abstract

Syntheses of N-Boc (S)-4-(diethylphosphono)-(α-methyl) phenylalanine [Boc-(α-Me) Phe (4- PO3Et2)-OH]() and N-Boc (S)-2-amino-6-(diethylphosphono) tetralin-2-carboxylic acid [Boc- Atc (6-PO3Et2)-OH]() are reported as conformationally-constrained phosphotyrosyl mimetics suitably protected for peptide synthesis. Both syntheses proceeded through chiral arylhalides that are converted to arylphosphonates by palladium-catalyzed cross coupling ...