ASYMMETRIC-SYNTHESIS OF IBUPROFEN AND KETOPROFEN

被引:12
作者
HAMON, DPG
MASSYWESTROPP, RA
NEWTON, JL
机构
[1] Department of Organic Chemistry, University of Adelaide, Adelaide, SA 5001
关键词
D O I
10.1016/S0957-4166(00)80334-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(S)-2-[4'-(2''-Methylpropyl)phenyl]propanoic acid (ibuprofen) and (S)-2-(3'-benzoylphenyl)propanoic acid (ketoprofen) have been synthesis in high enantiomeric excess. Control of the stereochemistry was achieved by a combination of Sharpless epoxidation followed by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond.
引用
收藏
页码:1435 / 1438
页数:4
相关论文
共 8 条
[1]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[2]   ENANTIOSELECTIVE SYNTHESES OF 2-ARYLPROPANOIC ACIDS - (S)-2-PHENYLPROPANOIC ACID [J].
COGHLAN, DR ;
HAMON, DPG ;
MASSYWESTROPP, RA ;
SLOBEDMAN, D .
TETRAHEDRON-ASYMMETRY, 1990, 1 (05) :299-302
[3]  
COMISSO G, 1980, GAZZ CHIM ITAL, V110, P123
[4]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[5]   ISOMERIC INVERSION OF IBUPROFEN (R)-ENANTIOMER IN HUMANS [J].
KAISER, DG ;
VANGIESSEN, GJ ;
REISCHER, RJ ;
WECHTER, WJ .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1976, 65 (02) :269-273
[7]   RECENT DEVELOPMENTS IN THE SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-ARYLPROPANOIC ACIDS - AN IMPORTANT CLASS OF NONSTEROIDAL ANTIINFLAMMATORY AGENTS [J].
SONAWANE, HR ;
BELLUR, NS ;
AHUJA, JR ;
KULKARNI, DG .
TETRAHEDRON-ASYMMETRY, 1992, 3 (02) :163-192
[8]   ENANTIODIVERGENT SYNTHESIS OF BOTH ENANTIOMERS OF IBUPROFEN FROM (2S,3S)-3-PHENYLGLYCIDOL [J].
TAKANO, S ;
YANASE, M ;
OGASAWARA, K .
HETEROCYCLES, 1989, 29 (09) :1849-1853