An efficient, highly enantioenriched route to L-carnitine and α-lipoic acid via hydrolytic kinetic resolution

被引：18

作者：

Bose, D. Sublias ^{[1
]}

Fatima, Liyakat ^{[1
]}

Rajender, Salla ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Fine Chem Lab, Div Organ Chem 3, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNTHESIS-STUTTGART | 2006年 / 11卷 / 11期

关键词：

L-carnitine; alpha-lipoic acid; hydrolytic kinetic resolution; terminal epoxide; enantioenriched;

D O I：

10.1055/s-2006-942363

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and practical approach for the synthesis of C-4 chiral building blocks using Jacobsen's hydrolytic kinetic resolution technique to resolve terminal epoxides and diols in high enantiomeric excess and excellent yields is described. The utilization of these building blocks for the synthesis of biologically important natural products L-carnitine and alpha-lipoic acid is illustrated.

引用

收藏

页码：1863 / 1867

页数：5

相关论文

共 43 条

[21]

Katsuki T., 2000, CATALYTIC ASYMMETRIC, P287

[22] Commercialization of the hydrolytic kinetic resolution of racemic epoxides: toward the economical large-scale production of enantiopure epichlorohydrin [J].

Larrow, JF ;

Hemberger, KE ;

Jasmin, S ;

Kabir, H ;

Morel, P .

TETRAHEDRON-ASYMMETRY, 2003, 14 (22) :3589-3592

[23] A FACILE AND HIGHLY STEREOSELECTIVE SYNTHESIS OF (R)[2-(PHENYLMETHOXY)ETHYL]OXIRANE AND (S)-[2-(PHENYLMETHOXY)ETHYL]OXIRANE [J].

LIU, C ;

COWARD, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2262-2264

[24] STEREOSPECIFIC SYNTHESIS OF (R)-S-ADENOSYL-1,8-DIAMINO-3-THIOOCTANE AND (S)-S-ADENOSYL-1,8-DIAMINO-3-THIOOCTANE, A POTENT INHIBITOR OF POLYAMINE BIOSYNTHESIS - COMPARISON OF ASYMMETRIC INDUCTION VS ENANTIOMERIC SYNTHESIS [J].

LIU, C ;

COWARD, JK .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (07) :2094-2101

[25] An efficient synthesis of (3R)-4-amino-3-hydroxy butyric acid (GABOB) via cyclic sulfite methodology [J].

Lohray, BB ;

Reddy, AS ;

Bhushan, V .

TETRAHEDRON-ASYMMETRY, 1996, 7 (08) :2411-2416

[26] SYNTHETIC STUDIES RELATED TO COMPACTIN AND MEVINOLIN - A NEW SYNTHESIS OF THE LACTONE SYSTEM [J].

MAJEWSKI, M ;

CLIVE, DLJ ;

ANDERSON, PC .

TETRAHEDRON LETTERS, 1984, 25 (20) :2101-2104

[27] STEREOCONTROLLED CONVERGENT SYNTHESIS OF 1,3-POLYOL [J].

NAKATA, T ;

SUENAGA, T ;

OISHI, T .

TETRAHEDRON LETTERS, 1989, 30 (47) :6525-6528

[28] Catalytic asymmetric epoxidation of α,β-unsaturated carbonyl compounds [J].

Nemoto, T ;

Ohshima, T ;

Shibasaki, M .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2002, 60 (02) :94-105

[29] ENANTIOSELECTIVE SYNTHESIS OF R-(+)-ALPHA-LIPOIC ACID [J].

PAGE, PCB ;

RAYNER, CM ;

SUTHERLAND, IO .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (18) :1408-1409

[30] Asymmetric epoxidation of electron-deficient olefins [J].

Porter, MJ ;

Skidmore, J .

CHEMICAL COMMUNICATIONS, 2000, (14) :1215-1225

← 1 2 3 4 5 →