STEREOSELECTIVE FUNCTIONALIZATION OF N-BOC PYROAMINOADIPIC ACID - SYNTHESIS OF 5-SUBSTITUTED AMINOADIPIC AND PIPECOLIC ACIDS

被引:24
作者
EZQUERRA, J
PEDREGAL, C
ESCRIBANO, A
CARRENO, MC
RUANO, JLG
机构
[1] CTR INVEST LILLY,E-28130 VALDEOLMOS,SPAIN
[2] UNIV AUTONOMA MADRID,DEPT QUIM ORGAN,E-28049 MADRID,SPAIN
关键词
D O I
10.1016/0040-4039(95)00456-M
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-Alkylsubstituted aminoadipic and pipecolic acids were diasteroselectively synthetized from methyl N-Boc pyrominoadipate.
引用
收藏
页码:3247 / 3250
页数:4
相关论文
共 19 条
[1]   SYNTHESIS AND NMDA ANTAGONISTIC PROPERTIES OF THE ENANTIOMERS OF 4-(3-PHOSPHONOPROPYL)PIPERAZINE-2-CARBOXYLIC ACID (CPP) AND OF THE UNSATURATED ANALOG (E)-4-(3-PHOSPHONOPROP-2-ENYL)PIPERAZINE-2-CARBOXYLIC ACID (CPP-ENE) [J].
AEBISCHER, B ;
FREY, P ;
HAERTER, HP ;
HERRLING, PL ;
MUELLER, W ;
OLVERMAN, HJ ;
WATKINS, JC .
HELVETICA CHIMICA ACTA, 1989, 72 (05) :1043-1051
[2]   ANTAGONISM OF EXCITATORY AMINO ACID-INDUCED RESPONSES AND OF SYNAPTIC EXCITATION IN THE ISOLATED SPINAL-CORD OF THE FROG [J].
EVANS, RH ;
FRANCIS, AA ;
HUNT, K ;
OAKES, DJ ;
WATKINS, JC .
BRITISH JOURNAL OF PHARMACOLOGY, 1979, 67 (04) :591-603
[3]   MG2+-LIKE SELECTIVE ANTAGONISM OF EXCITATORY AMINO ACID-INDUCED RESPONSES BY ALPHA-EPSILON-DIAMINOPIMELIC ACID, D-ALPHA-AMINOADIPATE AND HA-966 IN ISOLATED SPINAL-CORD OF FROG AND IMMATURE RAT [J].
EVANS, RH ;
FRANCIS, AA ;
WATKINS, JC .
BRAIN RESEARCH, 1978, 148 (02) :536-542
[4]   STEREOSELECTIVE DOUBLE ALKYLATION OF ETHYL N-BOC-PYROGLUTAMATE [J].
EZQUERRA, J ;
PEDREGAL, C ;
RUBIO, A ;
VAQUERO, JJ ;
MATIA, MP ;
MARTIN, J ;
DIAZ, A ;
NAVIO, JLG ;
DEETER, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4327-4331
[5]   STEREOSELECTIVE REACTIONS OF LITHIUM ENOLATES DERIVED FROM N-BOC PROTECTED PYROGLUTAMIC ESTERS [J].
EZQUERRA, J ;
PEDREGAL, C ;
RUBIO, A ;
YRURETAGOYENA, B ;
ESCRIBANO, A ;
SANCHEZFERRANDO, F .
TETRAHEDRON, 1993, 49 (38) :8665-8678
[6]  
EZQUERRA J, IN PRESS J ORG CHEM
[7]   CGP-37849 AND CGP-39551 - NOVEL AND POTENT COMPETITIVE N-METHYL-D-ASPARTATE RECEPTOR ANTAGONISTS WITH ORAL ACTIVITY [J].
FAGG, GE ;
OLPE, HR ;
POZZA, MF ;
BAUD, J ;
STEINMANN, M ;
SCHMUTZ, M ;
PORTET, C ;
BAUMANN, P ;
THEDINGA, K ;
BITTIGER, H ;
ALLGEIER, H ;
HECKENDORN, R ;
ANGST, C ;
BRUNDISH, D ;
DINGWALL, JG .
BRITISH JOURNAL OF PHARMACOLOGY, 1990, 99 (04) :791-797
[8]   A MILD 2-STEP METHOD FOR THE HYDROLYSIS METHANOLYSIS OF SECONDARY AMIDES AND LACTAMS [J].
FLYNN, DL ;
ZELLE, RE ;
GRIECO, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) :2424-2426
[9]   EXCITATORY AMINO-ACIDS AND ALZHEIMERS-DISEASE [J].
GREENAMYRE, JT ;
YOUNG, AB .
NEUROBIOLOGY OF AGING, 1989, 10 (05) :593-602
[10]  
GREENAMYRE JT, 1991, ARCH NEUROL-CHICAGO, P977