NEUROMEDIATOR ANALOGS - SYNTHESIS OF CIS (2R,3S) AND TRANS (2S,3S)-2,3-PIPERIDINE DICARBOXYLIC-ACIDS FROM (2S)-2-PHENYLGLYCINOL

被引：23

作者：

AGAMI, C ^{[1
]}

KADOURIPUCHOT, C ^{[1
]}

LEGUEN, V ^{[1
]}

VAISSERMANN, J ^{[1
]}

机构：

[1] UNIV PARIS 06,CNRS,CHIM MET TRANSIT LAB,F-75005 PARIS,FRANCE

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 10期

关键词：

D O I：

10.1016/0040-4039(95)00088-T

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cis and trans isomers of 2,3-piperidine dicarboxylic acids were obtained in enantiopure forms from the same chiral inductor: 2-phenylglycinol. This synthesis was mainly based on a delta-lactam formation via Stille's aza-annulation/hydrogenation procedure which includes here an asymmetric induction.

引用

页码：1657 / 1660

页数：4

共 16 条

[1] SYNTHESIS OF A REPRESENTATIVE CIS-TRANS PAIR OF 4,5-DISUBSTITUTED CYCLOPENTENYLLITHIUM REAGENTS
BARTH, W
PAQUETTE, LA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (14) : 2438 - 2443
[2] BORCH RF, 1968, TETRAHEDRON LETT, P61
[3] AZA-ANNULATION AS A ROUTE TO HYDROXYLATED ALKALOID LIPIDS - THE SYNTHESIS OF (+/-)-PROSOPININE
COOK, GR
BEHOLZ, LG
STILLE, JR
[J]. TETRAHEDRON LETTERS, 1994, 35 (11) : 1669 - 1672
[4] CONSTRUCTION OF HYDROXYLATED ALKALOIDS (+/-)-MANNONOLACTAM, (+/-)-DEOXYMANNOJIRIMYCIN, AND (+/-)-PROSOPININE THROUGH AZA-ANNULATION
COOK, GR
BEHOLZ, LG
STILLE, JR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) : 3575 - 3584
[5] CONFORMATIONAL ASPECTS OF THE ACTIONS OF SOME PIPERIDINE DICARBOXYLIC-ACIDS AT EXCITATORY AMINO-ACID RECEPTORS IN THE MAMMALIAN AND AMPHIBIAN SPINAL-CORD
DAVIES, J
EVANS, RH
FRANCIS, AA
JONES, AW
SMITH, DAS
WATKINS, JC
[J]. NEUROCHEMICAL RESEARCH, 1982, 7 (09) : 1119 - 1133
[6] IMINIUM SALTS FROM ALPHA-AMINO-ACID DECARBONYLATION - APPLICATION TO THE SYNTHESIS OF OCTAHYDROINDOLO[2,3-A]QUINOLIZINES
JOHANSEN, JE
CHRISTIE, BD
RAPOPORT, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) : 4914 - 4920
[7] SYNTHESES OF THE BRANCHED 9 CARBON UNIT OF THE TYPE-A STREPTOGRAMINS AND OTHER ANTIBIOTICS
KAZMIERCZAK, F
HELQUIST, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) : 3988 - 3992
[8] RELATIONSHIP BETWEEN STRUCTURE, CONFORMATIONAL FLEXIBILITY, AND BIOLOGICAL-ACTIVITY OF AGONISTS AND ANTAGONISTS AT THE N-METHYL-D-ASPARTIC ACID SUBTYPE OF EXCITATORY AMINO-ACID RECEPTORS
MADSEN, U
BREHM, L
SCHAUMBURG, K
JORGENSEN, FS
KROGSGAARDLARSEN, P
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) : 374 - 380
[9] STRUCTURE ACTIVITY RELATIONS OF N-METHYL-D-ASPARTATE RECEPTOR LIGANDS AS STUDIED BY THEIR INHIBITION OF [H-3]D-2-AMINO-5-PHOSPHONOPENTANOIC ACID BINDING IN RAT-BRAIN MEMBRANES
OLVERMAN, HJ
JONES, AW
MEWETT, KN
WATKINS, JC
[J]. NEUROSCIENCE, 1988, 26 (01) : 17 - 31
[10] DECAHYDROQUINOLINE CONSTRUCTION THROUGH AZA-ANNULATION - A STEREOSELECTIVE SYNTHESIS OF (+/-)-5-EPIPUMILIOTOXIN-C
PAULVANNAN, K
STILLE, JR
[J]. TETRAHEDRON LETTERS, 1993, 34 (42) : 6673 - 6676

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