Synthesis of enantiomerically pure (2R, 5S)- and (2R, 5R)-5-hydroxypipecolic acid from glycinate Schiff bases.

被引：40

作者：

Hoarau, S ^{[1
]}

Fauchere, JL ^{[1
]}

Pappalardo, L ^{[1
]}

Roumestant, ML ^{[1
]}

Viallefont, P ^{[1
]}

机构：

[1] INST RECH SERVIER, F-92150 SURESNES, FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 09期

关键词：

D O I：

10.1016/0957-4166(96)00332-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An asymmetric synthesis of cis- and trans-5-hydroxy-(D)pipecolic acid, starting from glycinate Schiff bases is described. The approach involves the stereoselective alkylation to generate an unsaturated side chain which on cyclisation leads to the desired trans- or cis- 5-hydroxy-(D)-pipecolic acid. Copyright (C) 1996 Elsevier Science Ltd

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页码：2585 / 2593

页数：9

相关论文

共 24 条

[1] CHIRAL SYNTHESIS OF 5-HYDROXY-(L)-PIPECOLIC ACIDS FROM (L)-GLUTAMIC ACID [J].

BAILEY, PD ;

BRYANS, JS .

TETRAHEDRON LETTERS, 1988, 29 (18) :2231-2234

[2] A HIGHLY REGIOSELECTIVE CONVERSION OF EPOXIDES TO HALOHYDRINS BY LITHIUM HALIDES [J].

BAJWA, JS ;

ANDERSON, RC .

TETRAHEDRON LETTERS, 1991, 32 (26) :3021-3024

[3]

BEYERMAN HC, 1959, RECL TRAV CHIM PAY B, V78, P648

[4]

CALLENS REA, 1982, B SOC CHIM BELG, V91, P713

[5] AN EFFICIENT ONE-STEP SYNTHESIS OF TERT-BUTYL GLYCINATE AND TERT-BUTYL SARCOSINATE [J].

CAVELIER, F ;

ROLLAND, M ;

VERDUCCI, J .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1994, 26 (05) :608-610

[6] SUBSTITUTION OF PROLINE WITH PIPECOLIC ACID AT THE SCISSILE BOND CONVERTS A PEPTIDE SUBSTRATE OF HIV PROTEINASE INTO A SELECTIVE INHIBITOR [J].

COPELAND, TD ;

WONDRAK, EM ;

TOZSER, J ;

ROBERTS, MM ;

OROSZLAN, S .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 169 (01) :310-314

[7] L-CIS-5-HYDROXYPIPECOLIC ACID FROM SEEDS OF GYMNOCLADUS-DIOICUS [J].

DESPONTIN, J ;

MARLIER, M ;

DARDENNE, G .

PHYTOCHEMISTRY, 1977, 16 (03) :387-388

[8]

FOWDEN L., 1970, Progress in phytochemistry, V2, P203

[9] PHARMACOLOGICAL PROFILE OF A HIGH-AFFINITY DIPEPTIDE NK1-RECEPTOR ANTAGONIST, FK888 [J].

FUJII, T ;

MURAI, M ;

MORIMOTO, H ;

MAEDA, Y ;

YAMAOKA, M ;

HAGIWARA, D ;

MIYAKE, H ;

IKARI, N ;

MATSUO, M .

BRITISH JOURNAL OF PHARMACOLOGY, 1992, 107 (03) :785-789

[10] CONVERSION OF BAIKIAIN TO TRANS-5-+ TRANS-4-HYDROXYPIPECOLIC ACIDS BY HYDROBORATION [J].

FUJITA, Y ;

IRREVERRE, F ;

WITKOP, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (09) :1844-&