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Novel enantioselective synthesis of (2S,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl)glycine (DCG-IV)
被引:14
作者
:
论文数:
引用数:
h-index:
机构:
Marinozzi, M
[
1
]
Pellicciari, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Perugia, Dipartimento Chim & Tecnol Farm, I-06123 Perugia, Italy
Univ Perugia, Dipartimento Chim & Tecnol Farm, I-06123 Perugia, Italy
Pellicciari, R
[
1
]
机构
:
[1]
Univ Perugia, Dipartimento Chim & Tecnol Farm, I-06123 Perugia, Italy
来源
:
TETRAHEDRON LETTERS
|
2000年
/ 41卷
/ 47期
关键词
:
metabotropic glutamate receptors;
(carboxycyclopropyl)glycines;
asymmetric cyclopropanation;
D O I
:
10.1016/S0040-4039(00)01629-4
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
A novel enantioselective synthesis of (2S,2'R,3'R)-2-(2',3'-dicarboxycyclopropyl)glycine (DCG-IV), a potent group II mGluRs agonist is described. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9125 / 9128
页数:4
相关论文
共 17 条
[1]
Anticonvulsant and glutamate release-inhibiting properties of the highly potent metabotropic glutamate receptor agonist (2S,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl) glycine (DCG-IV)
[J].
Attwell, PJE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Biochem, London SW7 2AZ, England
Attwell, PJE
;
Kent, NS
论文数:
0
引用数:
0
h-index:
0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Biochem, London SW7 2AZ, England
Kent, NS
;
Jane, DE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Biochem, London SW7 2AZ, England
Jane, DE
;
Croucher, MJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Biochem, London SW7 2AZ, England
Croucher, MJ
;
Bradford, HF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Biochem, London SW7 2AZ, England
Bradford, HF
.
BRAIN RESEARCH,
1998,
805
(1-2)
:138
-143
[2]
Comparative effect of L-CCG-I, DCG-IV and γ-carboxy-L-glutamate on all cloned metabotropic glutamate receptor subtypes
[J].
Brabet, I
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, INSERM, Ctr Pharmacol Endocrinol, UPR 9023, F-34094 Montpellier 5, France
Brabet, I
;
Parmentier, ML
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, INSERM, Ctr Pharmacol Endocrinol, UPR 9023, F-34094 Montpellier 5, France
Parmentier, ML
;
De Colle, C
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, INSERM, Ctr Pharmacol Endocrinol, UPR 9023, F-34094 Montpellier 5, France
De Colle, C
;
Bockaert, J
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, INSERM, Ctr Pharmacol Endocrinol, UPR 9023, F-34094 Montpellier 5, France
Bockaert, J
;
论文数:
引用数:
h-index:
机构:
Acher, F
;
Pin, JP
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, INSERM, Ctr Pharmacol Endocrinol, UPR 9023, F-34094 Montpellier 5, France
Pin, JP
.
NEUROPHARMACOLOGY,
1998,
37
(08)
:1043
-1051
[3]
ALPHA-PHENYLGLYCINOL AS CHIRAL AUXILIARY IN DIASTEREOSELECTIVE STRECKER SYNTHESIS OF ALPHA-AMINO-ACIDS
[J].
CHAKRABORTY, TK
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Institute of Chemical Technology, Hyderabad
CHAKRABORTY, TK
;
HUSSAIN, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Institute of Chemical Technology, Hyderabad
HUSSAIN, KA
;
REDDY, GV
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Institute of Chemical Technology, Hyderabad
REDDY, GV
.
TETRAHEDRON,
1995,
51
(33)
:9179
-9190
[4]
ACYCLIC STEREOSELECTION IN THE ALKYLATION OF CHIRAL DIPOLE-STABILIZED ORGANOLITHIUMS - A SELF-IMMOLATIVE CHIRALITY TRANSFER PROCESS FOR THE SYNTHESIS OF PRIMARY AMINES
[J].
GAWLEY, RE
论文数:
0
引用数:
0
h-index:
0
GAWLEY, RE
;
REIN, K
论文数:
0
引用数:
0
h-index:
0
REIN, K
;
CHEMBURKAR, S
论文数:
0
引用数:
0
h-index:
0
CHEMBURKAR, S
.
JOURNAL OF ORGANIC CHEMISTRY,
1989,
54
(13)
:3002
-3004
[5]
ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE AND DIVERSELY FUNCTIONALIZED CYCLOPROPANES
[J].
HANESSIAN, S
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Université de Montréal, Montreal, Quebec, H3C 3J7, P.O. Box 6128, Station Centre-ville
HANESSIAN, S
;
ANDREOTTI, D
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Université de Montréal, Montreal, Quebec, H3C 3J7, P.O. Box 6128, Station Centre-ville
ANDREOTTI, D
;
GOMTSYAN, A
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Université de Montréal, Montreal, Quebec, H3C 3J7, P.O. Box 6128, Station Centre-ville
GOMTSYAN, A
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1995,
117
(41)
:10393
-10394
[6]
A POTENT METABOTROPIC GLUTAMATE RECEPTOR AGONIST - ELECTROPHYSIOLOGICAL ACTIONS OF A CONFORMATIONALLY RESTRICTED GLUTAMATE ANALOG IN THE RAT SPINAL-CORD AND XENOPUS OOCYTES
[J].
ISHIDA, M
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI,3-18-22 HONKOMAGOME,BUNKYO KU,TOKYO 113,JAPAN
ISHIDA, M
;
AKAGI, H
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI,3-18-22 HONKOMAGOME,BUNKYO KU,TOKYO 113,JAPAN
AKAGI, H
;
SHIMAMOTO, K
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI,3-18-22 HONKOMAGOME,BUNKYO KU,TOKYO 113,JAPAN
SHIMAMOTO, K
;
OHFUNE, Y
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI,3-18-22 HONKOMAGOME,BUNKYO KU,TOKYO 113,JAPAN
OHFUNE, Y
;
SHINOZAKI, H
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI,3-18-22 HONKOMAGOME,BUNKYO KU,TOKYO 113,JAPAN
SHINOZAKI, H
.
BRAIN RESEARCH,
1990,
537
(1-2)
:311
-314
[7]
A NOVEL METABOTROPIC GLUTAMATE-RECEPTOR AGONIST - MARKED DEPRESSION OF MONOSYNAPTIC EXCITATION IN THE NEWBORN RAT ISOLATED SPINAL-CORD
[J].
ISHIDA, M
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI, 3-18-22 HONKOMAGOME, BUNKYO KU, TOKYO 113, JAPAN
ISHIDA, M
;
SAITOH, T
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI, 3-18-22 HONKOMAGOME, BUNKYO KU, TOKYO 113, JAPAN
SAITOH, T
;
SHIMAMOTO, K
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI, 3-18-22 HONKOMAGOME, BUNKYO KU, TOKYO 113, JAPAN
SHIMAMOTO, K
;
OHFUNE, Y
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI, 3-18-22 HONKOMAGOME, BUNKYO KU, TOKYO 113, JAPAN
OHFUNE, Y
;
SHINOZAKI, H
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI, 3-18-22 HONKOMAGOME, BUNKYO KU, TOKYO 113, JAPAN
SHINOZAKI, H
.
BRITISH JOURNAL OF PHARMACOLOGY,
1993,
109
(04)
:1169
-1177
[8]
LIPTON MF, 1988, ORG SYNTH, V50-9, P492
[9]
Stereochemically controlled cyclopropanation of (S)-glyceraldehyde acetonide-derived olefins.: Synthesis of (2S,1′R,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl)glycine
[J].
Ma, DW
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Ma, DW
;
Cao, YY
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Cao, YY
;
Yang, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Yang, Y
;
Cheng, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Cheng, DL
.
ORGANIC LETTERS,
1999,
1
(02)
:285
-287
[10]
OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE
[J].
MANCUSO, AJ
论文数:
0
引用数:
0
h-index:
0
机构:
TEMPLE UNIV,FELS RES INST,PHILADELPHIA,PA 19122
MANCUSO, AJ
;
HUANG, SL
论文数:
0
引用数:
0
h-index:
0
机构:
TEMPLE UNIV,FELS RES INST,PHILADELPHIA,PA 19122
HUANG, SL
;
SWERN, D
论文数:
0
引用数:
0
h-index:
0
机构:
TEMPLE UNIV,FELS RES INST,PHILADELPHIA,PA 19122
SWERN, D
.
JOURNAL OF ORGANIC CHEMISTRY,
1978,
43
(12)
:2480
-2482
←
1
2
→
共 17 条
[1]
Anticonvulsant and glutamate release-inhibiting properties of the highly potent metabotropic glutamate receptor agonist (2S,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl) glycine (DCG-IV)
[J].
Attwell, PJE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Biochem, London SW7 2AZ, England
Attwell, PJE
;
Kent, NS
论文数:
0
引用数:
0
h-index:
0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Biochem, London SW7 2AZ, England
Kent, NS
;
Jane, DE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Biochem, London SW7 2AZ, England
Jane, DE
;
Croucher, MJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Biochem, London SW7 2AZ, England
Croucher, MJ
;
Bradford, HF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Biochem, London SW7 2AZ, England
Bradford, HF
.
BRAIN RESEARCH,
1998,
805
(1-2)
:138
-143
[2]
Comparative effect of L-CCG-I, DCG-IV and γ-carboxy-L-glutamate on all cloned metabotropic glutamate receptor subtypes
[J].
Brabet, I
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, INSERM, Ctr Pharmacol Endocrinol, UPR 9023, F-34094 Montpellier 5, France
Brabet, I
;
Parmentier, ML
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, INSERM, Ctr Pharmacol Endocrinol, UPR 9023, F-34094 Montpellier 5, France
Parmentier, ML
;
De Colle, C
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, INSERM, Ctr Pharmacol Endocrinol, UPR 9023, F-34094 Montpellier 5, France
De Colle, C
;
Bockaert, J
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, INSERM, Ctr Pharmacol Endocrinol, UPR 9023, F-34094 Montpellier 5, France
Bockaert, J
;
论文数:
引用数:
h-index:
机构:
Acher, F
;
Pin, JP
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, INSERM, Ctr Pharmacol Endocrinol, UPR 9023, F-34094 Montpellier 5, France
Pin, JP
.
NEUROPHARMACOLOGY,
1998,
37
(08)
:1043
-1051
[3]
ALPHA-PHENYLGLYCINOL AS CHIRAL AUXILIARY IN DIASTEREOSELECTIVE STRECKER SYNTHESIS OF ALPHA-AMINO-ACIDS
[J].
CHAKRABORTY, TK
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Institute of Chemical Technology, Hyderabad
CHAKRABORTY, TK
;
HUSSAIN, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Institute of Chemical Technology, Hyderabad
HUSSAIN, KA
;
REDDY, GV
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Institute of Chemical Technology, Hyderabad
REDDY, GV
.
TETRAHEDRON,
1995,
51
(33)
:9179
-9190
[4]
ACYCLIC STEREOSELECTION IN THE ALKYLATION OF CHIRAL DIPOLE-STABILIZED ORGANOLITHIUMS - A SELF-IMMOLATIVE CHIRALITY TRANSFER PROCESS FOR THE SYNTHESIS OF PRIMARY AMINES
[J].
GAWLEY, RE
论文数:
0
引用数:
0
h-index:
0
GAWLEY, RE
;
REIN, K
论文数:
0
引用数:
0
h-index:
0
REIN, K
;
CHEMBURKAR, S
论文数:
0
引用数:
0
h-index:
0
CHEMBURKAR, S
.
JOURNAL OF ORGANIC CHEMISTRY,
1989,
54
(13)
:3002
-3004
[5]
ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE AND DIVERSELY FUNCTIONALIZED CYCLOPROPANES
[J].
HANESSIAN, S
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Université de Montréal, Montreal, Quebec, H3C 3J7, P.O. Box 6128, Station Centre-ville
HANESSIAN, S
;
ANDREOTTI, D
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Université de Montréal, Montreal, Quebec, H3C 3J7, P.O. Box 6128, Station Centre-ville
ANDREOTTI, D
;
GOMTSYAN, A
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Université de Montréal, Montreal, Quebec, H3C 3J7, P.O. Box 6128, Station Centre-ville
GOMTSYAN, A
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1995,
117
(41)
:10393
-10394
[6]
A POTENT METABOTROPIC GLUTAMATE RECEPTOR AGONIST - ELECTROPHYSIOLOGICAL ACTIONS OF A CONFORMATIONALLY RESTRICTED GLUTAMATE ANALOG IN THE RAT SPINAL-CORD AND XENOPUS OOCYTES
[J].
ISHIDA, M
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI,3-18-22 HONKOMAGOME,BUNKYO KU,TOKYO 113,JAPAN
ISHIDA, M
;
AKAGI, H
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI,3-18-22 HONKOMAGOME,BUNKYO KU,TOKYO 113,JAPAN
AKAGI, H
;
SHIMAMOTO, K
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI,3-18-22 HONKOMAGOME,BUNKYO KU,TOKYO 113,JAPAN
SHIMAMOTO, K
;
OHFUNE, Y
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI,3-18-22 HONKOMAGOME,BUNKYO KU,TOKYO 113,JAPAN
OHFUNE, Y
;
SHINOZAKI, H
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI,3-18-22 HONKOMAGOME,BUNKYO KU,TOKYO 113,JAPAN
SHINOZAKI, H
.
BRAIN RESEARCH,
1990,
537
(1-2)
:311
-314
[7]
A NOVEL METABOTROPIC GLUTAMATE-RECEPTOR AGONIST - MARKED DEPRESSION OF MONOSYNAPTIC EXCITATION IN THE NEWBORN RAT ISOLATED SPINAL-CORD
[J].
ISHIDA, M
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI, 3-18-22 HONKOMAGOME, BUNKYO KU, TOKYO 113, JAPAN
ISHIDA, M
;
SAITOH, T
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI, 3-18-22 HONKOMAGOME, BUNKYO KU, TOKYO 113, JAPAN
SAITOH, T
;
SHIMAMOTO, K
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI, 3-18-22 HONKOMAGOME, BUNKYO KU, TOKYO 113, JAPAN
SHIMAMOTO, K
;
OHFUNE, Y
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI, 3-18-22 HONKOMAGOME, BUNKYO KU, TOKYO 113, JAPAN
OHFUNE, Y
;
SHINOZAKI, H
论文数:
0
引用数:
0
h-index:
0
机构:
TOKYO METROPOLITAN INST MED SCI, 3-18-22 HONKOMAGOME, BUNKYO KU, TOKYO 113, JAPAN
SHINOZAKI, H
.
BRITISH JOURNAL OF PHARMACOLOGY,
1993,
109
(04)
:1169
-1177
[8]
LIPTON MF, 1988, ORG SYNTH, V50-9, P492
[9]
Stereochemically controlled cyclopropanation of (S)-glyceraldehyde acetonide-derived olefins.: Synthesis of (2S,1′R,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl)glycine
[J].
Ma, DW
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Ma, DW
;
Cao, YY
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Cao, YY
;
Yang, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Yang, Y
;
Cheng, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Cheng, DL
.
ORGANIC LETTERS,
1999,
1
(02)
:285
-287
[10]
OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE
[J].
MANCUSO, AJ
论文数:
0
引用数:
0
h-index:
0
机构:
TEMPLE UNIV,FELS RES INST,PHILADELPHIA,PA 19122
MANCUSO, AJ
;
HUANG, SL
论文数:
0
引用数:
0
h-index:
0
机构:
TEMPLE UNIV,FELS RES INST,PHILADELPHIA,PA 19122
HUANG, SL
;
SWERN, D
论文数:
0
引用数:
0
h-index:
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机构:
TEMPLE UNIV,FELS RES INST,PHILADELPHIA,PA 19122
SWERN, D
.
JOURNAL OF ORGANIC CHEMISTRY,
1978,
43
(12)
:2480
-2482
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