SYNTHESIS OF (2S,4S) 2-CARBOXY-4-PYRROLIDINE ACETIC-ACID, A CONFORMATIONALLY CONSTRAINED 2-AMINO ADIPIC ACID ANALOG

被引:43
作者
LANGLOIS, N
ROJAS, A
机构
[1] Institut de Chimie des Substances Naturelles, C.N.R.S.
关键词
PYROGLUTAMIC ACID; EXCITATORY AMINO-ACIDS; ALKYL BROMOACETATE; SODIUM CYANOBOROHYDRIDE;
D O I
10.1016/S0040-4039(00)60445-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(2S,4S) 2-carboxy-4-pyrrolidine acetic acid was synthesized from (S) pyroglutamic acid in 26% overall yield by a regiospecific deprotonation of the N-methoxycarbonyl benzylester 4.
引用
收藏
页码:2477 / 2480
页数:4
相关论文
共 19 条
[1]   SYNTHESIS OF NEOTHRAMYCINS [J].
ANDRIAMIALISOA, RZ ;
LANGLOIS, N .
TETRAHEDRON LETTERS, 1986, 27 (10) :1149-1152
[2]   AMINO-ACID SYNTHESIS USING (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL [J].
BALDWIN, JE ;
MIRANDA, T ;
MOLONEY, M ;
HOKELEK, T .
TETRAHEDRON, 1989, 45 (23) :7459-7468
[3]   D-ALPHA-AMINOADIPATE AS A SELECTIVE ANTAGONIST OF AMINO ACID-INDUCED AND SYNAPTIC EXCITATION OF MAMMALIAN SPINAL NEURONS [J].
BISCOE, TJ ;
EVANS, RH ;
FRANCIS, AA ;
MARTIN, MR ;
WATKINS, JC .
NATURE, 1977, 270 (5639) :743-745
[4]   SYNTHESIS OF NON-PROTEINOGENIC AMINO-ACIDS WITH 3 CHIRAL CENTERS [J].
BOWLER, AN ;
DOYLE, PM ;
HITCHCOCK, PB ;
YOUNG, DW .
TETRAHEDRON LETTERS, 1991, 32 (23) :2679-2682
[5]   SIMPLE SYNTHESIS OF L-GAMMA-CARBOXYGLUTAMATE AND DERIVATIVES THEREOF [J].
DANISHEFSKY, S ;
BERMAN, E ;
CLIZBE, LA ;
HIRAMA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (15) :4385-4386
[6]   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
[7]   SYNTHESES OF (2S,4S)-4-SUBSTITUTED AND (2S,4R)-4-SUBSTITUTED GLUTAMIC-ACID ANALOGS FOR NEUROEXCITATORY ACTIVITY STUDIES [J].
HON, YS ;
CHANG, YC ;
GONG, ML .
HETEROCYCLES, 1990, 31 (02) :191-195
[8]   TOTAL SYNTHESIS OF ECHINOCANDINS .1. STEREOCONTROLLED SYNTHESES OF THE CONSTITUENT AMINO-ACIDS [J].
KUROKAWA, N ;
OHFUNE, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6041-6043
[9]   METHYLPYROGLUTAMATE AS CHIRAL SYNTHON - ASYMMETRIC-SYNTHESIS OF ANTIHYPERTENSIVE PYRROLIDINES [J].
LANGLOIS, N ;
ANDRIAMIALISOA, RZ .
TETRAHEDRON LETTERS, 1988, 29 (26) :3259-3262
[10]   A SHORT SYNTHESIS OF C-2 SYMMETRICAL (2S, 5S) PYRROLIDINE-2,5 DICARBOXYLIC-ACID, A CONSTITUENT OF RED ALGA SCHIZYMENIA-DUBYI [J].
LANGLOIS, N ;
ROJAS, A .
TETRAHEDRON, 1993, 49 (01) :77-82