
TY  - JOUR
A1  - Chiefari, J 
A1  - Galanopoulos, S 
A1  - Janowski, WK 
A1  - Kerr, DIB 
A1  - Prager, RH 
T1  - The Synthesis of Phosphonobaclofen, an Antagonist of Baclofen
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1987
VL  - 40
IS  - 9
SP  - 1511
EP  - 1518
KW  - 
UR  - https://doi.org/10.1071/CH9871511 
N2  - Phosphonobaclofen, 3-amino-2-(4-chlorophenyl) propylphosphonic acid, has been synthesized in five steps from ethyl 3-(4-chloropheny1)but-2-enoate, and is a specific antagonist of baclofen . Two alternative synthetic pathways, involving conjugate addition of phosphite to 2-(4-chlorophenyl) propenenitrile and of cyanide to 2-(4-chlorophenyl) ethenylphosphonate ester, failed. Cyanide ion did add efficiently to ethyl 3-(4-chloropheny1)-2-diethoxyphosphinylprop-2- enoate, and hydrogenation followed by hydrolysis of the product gave (2S,3S)- and (2R,3R)-4-amino-3-(4-chloropheny1)-2-phosphonobutanoic acid, which is also undergoing pharmacological evaluation. 
ER  -

