Facile synthesis of (2S,1'S,2'S)-2-(carboxycyclopropyl)glycine, an isotype-selective agonist of metabotropic glutamate receptors

被引：29

作者：

Ma, DW

Ma, ZC

机构：

[1] Stt. Key Lab. Bio-Organ. Nat. P., Shanghai Inst. of Organic Chemistry, Chinese Academy of Sciences, 345 Fenglin Lu

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 43期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/S0040-4039(97)10037-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2S,1'S,2'S)-2-(Carboxycyclopropyl)glycine (L-CCG-I) was synthesized in 12 steps and 14% overall yield by using Sharpless's asymmetric dihydroxylation reaction and stereochemically controlled cyclopropanation as key steps. (C) 1997 Elsevier Science Ltd.

引用

页码：7599 / 7602

页数：4

共 28 条

[1] SELECTIVE ASYMMETRIC DIHYDROXYLATION OF POLYENES [J].

BECKER, H ;

SOLER, MA ;

SHARPLESS, KB .

TETRAHEDRON, 1995, 51 (05) :1345-1376

[2] A STRAIGHTFORWARD SYNTHESIS OF (-)-(1S,2R)-ALLONORCORONAMIC ACID USING D-MANNITOL AS THE CHIRAL SOURCE [J].

CATIVIELA, C ;

DIAZDEVILLEGAS, MD ;

JIMENEZ, AI .

TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :2067-2072

[3] A SIMPLE SYNTHESIS OF (-)-(1S,2R)-ALLOCORONAMIC ACID IN ITS ENANTIOMERICALLY PURE FORM [J].

CATIVIELA, C ;

DIAZDEVILLEGAS, MD ;

JIMENEZ, AI .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :177-182

[4]

CHAUDHARY SK, 1979, TETRAHEDRON LETT, V2, P99

[5] Asymmetric synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740) [J].

Dominguez, C ;

Ezquerra, J ;

Prieto, L ;

Espada, M ;

Pedregal, C .

TETRAHEDRON-ASYMMETRY, 1997, 8 (04) :511-514

[6] ROLE OF A METABOTROPIC GLUTAMATE-RECEPTOR IN SYNAPTIC MODULATION IN THE ACCESSORY OLFACTORY-BULB [J].

HAYASHI, Y ;

MOMIYAMA, A ;

TAKAHASHI, T ;

OHISHI, H ;

OGAWAMEGURO, R ;

SHIGEMOTO, R ;

MIZUNO, N ;

NAKANISHI, S .

NATURE, 1993, 366 (6456) :687-690

[7] A NEW METABOTROPIC GLUTAMATE-RECEPTOR AGONIST - DEVELOPMENTAL-CHANGE OF ITS SENSITIVITY TO RECEPTORS IN THE NEWBORN RAT SPINAL-CORD [J].

ISHIDA, M ;

SAITOH, T ;

SHINOZAKI, H .

NEUROSCIENCE LETTERS, 1993, 160 (02) :156-158

[8]

JANE DE, 1994, BRIT J PHARMACOL, V112, P809

[9] INDUCTION OF AN OLFACTORY MEMORY BY THE ACTIVATION OF A METABOTROPIC GLUTAMATE-RECEPTOR [J].

KABA, H ;

HAYASHI, Y ;

HIGUCHI, T ;

NAKANISHI, S .

SCIENCE, 1994, 265 (5169) :262-264

[10] METABOTROPIC GLUTAMATE RECEPTORS : NOVEL TARGETS FOR DRUG DEVELOPMENT [J].

KNOEPFEL, T ;

KUHN, R ;

ALLGEIER, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (09) :1417-1426

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