A practical synthesis of optically active (R)-2-propyloctanoic acid:: Therapeutic agent for Alzheimer's disease

被引:67
作者
Hasegawa, T [1 ]
Yamamoto, H [1 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan
关键词
D O I
10.1246/bcsj.73.423
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(R)-2-Propyloctanoic acid has been developed as a novel therapeutic agent for Alzheimer's disease. A large-scale synthesis of this candidate was achieved by using Oppolzer's camphorsultam as a chiral auxiliary under improved conditions. It was essential for the successful synthesis of this compound to utilize a new removal method for the chiral source with a combination of tetrabutylammonium hydroxide and hydrogen peroxide. The present process afforded the desired product in high yield with high optical purity.
引用
收藏
页码:423 / 428
页数:6
相关论文
共 27 条
[1]  
Ager DJ, 1996, SYNTHESIS-STUTTGART, P1283
[2]  
CAVALLO AS, 1992, TETRAHEDRON, V48, P2453
[3]   ENANTIOSELECTIVE ALKYLATION OF CHIRAL ENOLATES [J].
EVANS, DA ;
TAKACS, JM .
TETRAHEDRON LETTERS, 1980, 21 (44) :4233-4236
[4]   ENANTIOSELECTIVE ALDOL CONDENSATIONS .3. ERYTHRO-SELECTIVE CONDENSATIONS VIA ZIRCONIUM ENOLATES [J].
EVANS, DA ;
MCGEE, LR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (10) :2876-2878
[5]   ENANTIOSELECTIVE MICHAEL REACTIONS - DIASTEREOSELECTIVE REACTIONS OF CHLOROTITANIUM ENOLATES OF CHIRAL N-ACYLOXAZOLIDINONES WITH REPRESENTATIVE ELECTROPHILIC OLEFINS [J].
EVANS, DA ;
BILODEAU, MT ;
SOMERS, TC ;
CLARDY, J ;
CHERRY, D ;
KATO, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5750-5752
[6]   ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].
EVANS, DA ;
ENNIS, MD ;
MATHRE, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739
[7]  
EVANS DA, 1982, ALDRICHIM ACTA, V15, P318
[8]   AZINOTHRICIN SYNTHETIC STUDIES .1. EFFICIENT ASYMMETRIC SYNTHESES OF (3R)-PIPERAZIC AND (3S)-PIPERAZIC ACIDS [J].
HALE, KJ ;
DELISSER, VM ;
MANAVIAZAR, S .
TETRAHEDRON LETTERS, 1992, 33 (49) :7613-7616
[9]  
Hasegawa T, 1998, SYNLETT, P882
[10]  
Hasegawa T, 1999, SYNLETT, P84