SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED CYCLIC ALPHA-AMINO-ACIDS STRUCTURALLY RELATED TO ACPD

被引：23

作者：

ALONSO, F

MICO, I

NAJERA, C

SANSANO, JM

YUS, M

EZQUERRA, J

YRURETAGOYENA, B

GRACIA, I

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALACANT,SPAIN

[2] CTR INVEST LILLY SA,E-28130 VALDEOLMOS,SPAIN

来源：

TETRAHEDRON | 1995年 / 51卷 / 37期

关键词：

D O I：

10.1016/0040-4020(95)00586-W

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of 3-substituted cyclopentanones 12-16, 4-substituted cyclohexanones 23-28 and cycloheptanones 38-41 is described. Substituents in the cycloalkanones are carboxylate, phosphonate or tetrazole groups, separated from the ring by a 0, 1, 2, or 3 carbon atoms chain. These cycloalkanones have been transformed into alpha-amino acids 9-11 by hydrolysis of the corresponding hydantoin derivatives 21, 37 and 62, obtained under Bucherer-Bergs reaction conditions.

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页码：10259 / 10280

页数：22

相关论文

共 25 条

[1] SYNTHESIS AND ACTIVITY OF A POTENT N-METHYL-D-ASPARTIC ACID AGONIST, TRANS-1-AMINOCYCLOBUTANE-1,3-DICARBOXYLIC ACID, AND RELATED PHOSPHONIC AND CARBOXYLIC-ACIDS [J].

ALLAN, RD ;

HANRAHAN, JR ;

HAMBLEY, TW ;

JOHNSTON, GAR ;

MEWETT, KN ;

MITROVIC, AD .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) :2905-2915

[2]

AVENDANO C, 1985, CHEM HYDANTOINS, V38, P177

[3] CYCLIC ANALOGS OF 2-AMINO-4-PHOSPHONOBUTANOIC ACID (APB) AND THEIR INHIBITION OF HIPPOCAMPAL EXCITATORY TRANSMISSION AND DISPLACEMENT OF [H-3] APB BINDING [J].

CROOKS, SL ;

ROBINSON, MB ;

KOERNER, JF ;

JOHNSON, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (10) :1988-1995

[4] SYNTHESIS, RESOLUTION, AND ABSOLUTE-CONFIGURATION OF THE ISOMERS OF THE NEURONAL EXCITANT 1-AMINO-1,3-CYCLOPENTANEDICARBOXYLIC ACID [J].

CURRY, K ;

PEET, MJ ;

MAGNUSON, DSK ;

MCLENNAN, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (04) :864-867

[5]

EZQUERRA J, 1995, TETRAHEDRON, V51, P3721

[6] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .10. "TRIMETHYLSILYLDIAZOMETHANE(TMSCHN2) - A NEW, STABLE, AND SAFE REAGENT FOR THE HOMOLOGATION OF KETONES [J].

HASHIMOTO, N ;

AOYAMA, T ;

SHIOIRI, T .

TETRAHEDRON LETTERS, 1980, 21 (48) :4619-4622

[7]

Hesse M., 1991, RING ENLARGEMENT ORG

[8] EXCITATORY AMINO-ACID NEUROTRANSMISSION [J].

JOHNSON, RL ;

KOERNER, JF .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (11) :2057-2066

[9] SYNTHESIS AND REACTIVITY TOWARD ACYL CHLORIDES AND ENONES OF THE NEW HIGHLY FUNCTIONALIZED COPPER REAGENTS RCU(CN)ZNI [J].

KNOCHEL, P ;

YEH, MCP ;

BERK, SC ;

TALBERT, J .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2390-2392

[10]

KOZIKOWSKI AP, 1991, NEUROBIOLOGY NMDA RE