An efficient synthesis of a 4 '-phosphonodifluoromethyl-3 '-formyl-phenylalanine containing Src SH2 ligand

Authors
Shakespeare, WC Bohacek, RS Narula, SS Azimioara, MD Yuan, RW Dalgarno, DC Madden, L Botfield, MC Holt, DA
Citation
Wc. Shakespeare et al., An efficient synthesis of a 4 '-phosphonodifluoromethyl-3 '-formyl-phenylalanine containing Src SH2 ligand, BIOORG MED, 9(21), 1999, pp. 3109-3112
Citations number
22
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
9
Issue
21
Year of publication
1999
Pages
3109 - 3112
Database
ISI
SICI code
0960-894X(19991101)9:21<3109:AESOA4>2.0.ZU;2-A
Abstract
A CuBr-mediated, regioselective cross-coupling between methyl 2,5-diiodoben zoate (4) and [(diethoxyphosphinyl)difluoromethyl]zinc bromide is reported. Palladium-catalyzed incorporation of an amino acid side chain, followed by subsequent modifications resulted in the rapid construction of 2. Compound 2 was designed to engage Cys188 of the Src SH2 domain, however, this was n ot observed spectroscopically. (C) 1999 Elsevier Science Ltd. All rights re served.