Asymmetric synthesis of (+)-(11R,12S)-mefloquine hydrochloride

被引：21

作者：

Xie Zhi-Xiang ^{[1
]}

Zhang Lu-Zhong ^{[1
]}

Ren Xiao-Juan ^{[1
]}

Tang Shi-Yang ^{[1
]}

Li Yang ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2008年 / 26卷 / 07期

关键词：

mefloquine; antimalarial drug; proline-catalyzed; Beckmann rearrangement; asymmetric synthesis;

D O I：

10.1002/cjoc.200890231

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric synthesis of (+)-(11R,12S)-mefloquine hydrochloride, an antimalarial drug, was accomplished from commercially available 2-trifluoromethylaniline, ethyl 4,4,4-trifluoroacetoacetate and cyclopentanone in 7 steps with a 14% overall yield. The key steps were proline-catalyzed asymmetric direct aldol reaction and Beckmann rearrangement. The absolute configuration was assigned by a Mosher's method.

引用

页码：1272 / 1276

页数：5

共 50 条

[1] TOTAL SYNTHESIS OF (11R,12S)-DIHETE
GIGOU, A
BEAUCOURT, JP
LELLOUCHE, JP
GREE, R
TETRAHEDRON LETTERS, 1991, 32 (05) : 635 - 638
[2] The synthesis of (11R,12S)-lactobacillic acid and its enantiomer
Coxon, GD
Al-Dulayymi, JR
Baird, MS
Knobl, S
Roberts, E
Minnikin, DE
TETRAHEDRON-ASYMMETRY, 2003, 14 (09) : 1211 - 1222
[3] A short catalytic enantioselective synthesis of the vascular antiinflammatory eicosanoid (11R,12S)-oxidoarachidonic acid
Han, XJ
Crane, SN
Corey, EJ
ORGANIC LETTERS, 2000, 2 (22) : 3437 - 3438
[4] (-) - (11R, 12S)-mefloquine ameliorates neuropathic pain by modulating Cx36-ER stress interaction in the pain-related central nervous system in rats
Gu, Lingling
Lai, Zelin
Zhang, Cheng
Liu, Zhili
Huo, Yan
Qian, Yu
Wang, Bingying
Wang, Zhiru
Zhao, Zheng
Hu, Wenhao
Ma, Mingliang
LIFE SCIENCES, 2025, 363
[5] Practical Asymmetric Synthesis of (+)-erythro Mefloquine Hydrochloride
Hems, William P.
Jackson, William P.
Nightingale, Peter
Bryant, Rob
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (03) : 461 - 463
[6] Total synthesis of (8S,11R,12R)- and (8R,11R,12R)-topsentolide B2 diastereomers and assignment of the absolute configuration
Fernandes, Rodney A.
Kattanguru, Pullaiah
TETRAHEDRON-ASYMMETRY, 2011, 22 (20-22) : 1930 - 1935
[7] Total Synthesis of Nominal (11S)- and (11R)-Cyclocinamide A
Garcia, Jessica M.
Curzon, Stephanie S.
Watts, Katharine R.
Konopelski, Joseph P.
ORGANIC LETTERS, 2012, 14 (08) : 2054 - 2057
[8] Synthesis of a prenylated and immunosuppressive marine galactosphingolipid with cyclopropane-containing alkyl chains:: (2S,3R,11S,12R,2′"R,5′"Z,11′"S,12′"R)-plakoside A and its (2S,3R,11R,12S,2′"R,5′"Z,11′"R,12′"S) isomer
Seki, M
Mori, K
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (20) : 3797 - 3809
[9] Enantiocontrolled synthesis of (11S,12S,13S)-(9Z,15Z)- and (11R,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxy octadecadienoic acids by means of the sharpless asymmetric epoxidation of the unsymmetrical divinylcarbinol
Honda, T
Ohta, M
Mizutani, H
HETEROCYCLES, 1997, 46 : 137 - 140
[10] AN EFFICIENT PROCEDURE FOR THE SYNTHESIS AND ISOLATION OF (+)-(2R,3R,11R,12R)-TETRAPHENYL-18-CROWN-6 AND (-)-(2S,3S,11S,12S)-TETRAPHENYL-18-CROWN-6
CROSBY, J
FAKLEY, ME
GEMMELL, C
MARTIN, K
QUICK, A
SLAWIN, AMZ
SHAHRIARIZAVAREH, H
STODDART, JF
WILLIAMS, DJ
TETRAHEDRON LETTERS, 1989, 30 (29) : 3849 - 3852

← 1 2 3 4 5 →