Approaches to a synthesis of α-kainic acid

被引：38

作者：

Cossy, J ^{[1
]}

Cases, M ^{[1
]}

Pardo, DG ^{[1
]}

机构：

[1] CNRS, Chim Organ Lab, ESPCI, F-75231 Paris 05, France

来源：

TETRAHEDRON | 1999年 / 55卷 / 19期

关键词：

asymmetric synthesis; cyclization; kainoids; radicals and radical reaction;

D O I：

10.1016/S0040-4020(99)00284-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Kainic acid A, first isolated in 1953 from the marine alga Digenea simplex,(1) is the parent member of the kainoids displaying potent anthelmintic properties and neurotransmitting activity(2,3) in the central nervous system. Among these properties, the neuroexcitatory activity is attributed to their trans C-2/C-3 : cis C-3/C-4 structure and the functionality at the C-4 center beside the 2-carboxy and 3-carboxymethyl functionalities.

引用

收藏

页码：6153 / 6166

页数：14

相关论文

共 42 条

[1] Stereoselective synthesis of (+/-)-alpha-kainic acid using free radical key reactions [J].

Bachi, MD ;

BarNer, N ;

Melman, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :7116-7124

[2]

Bachi MD, 1996, SYNLETT, P60

[3] Enantioselective total synthesis of (-)-alpha-kainic acid through free radical cyclization of an alkenyl monothioformimide [J].

Bachi, MD ;

Melman, A .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1896-1898

[4] COBALT-MEDIATED CYCLIZATION OF AMINO-ACID DERIVATIVES - APPLICATION TO THE KAINOIDS [J].

BALDWIN, JE ;

LI, CS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) :166-168

[5] ENANTIOSELECTIVE KAINOID SYNTHESIS BY COBALT-MEDIATED CYCLIZATION OF AN AMINO-ACID DERIVATIVE [J].

BALDWIN, JE ;

MOLONEY, MG ;

PARSONS, AF .

TETRAHEDRON, 1990, 46 (20) :7263-7282

[6] TOTAL SYNTHESIS OF THE TRIQUINANE MARINE SESQUITERPENE (PLUS-OR-MINUS)DELTA(9(12)) CAPNELLENE USING A PALLADIUM-CATALYZED BIS-CYCLIZATION STEP [J].

BALME, G ;

BOUYSSI, D .

TETRAHEDRON, 1994, 50 (02) :403-414

[7] A NEW APPROACH TO KAINOIDS THROUGH TANDEM MICHAEL REACTION METHODOLOGY - APPLICATION TO THE ENANTIOSELECTIVE SYNTHESIS OF (+)-ALPHA-ALLOKAINIC AND (-)-ALPHA-ALLOKAINIC ACID AND TO THE FORMAL SYNTHESIS OF (-)-ALPHA-KAINIC ACID [J].

BARCO, A ;

BENETTI, S ;

SPALLUTO, G ;

CASOLARI, A ;

POLLINI, GP ;

ZANIRATO, V .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6279-6286

[8] SYNTHESIS OF BICYCLIC CYCLOPENTANOLS BY PHOTOREDUCTIVE CYCLIZATION OF DELTA,EPSILON-UNSATURATED KETONES [J].

BELOTTI, D ;

COSSY, J ;

PETE, JP ;

PORTELLA, C .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) :4196-4200

[9] SYNTHESIS OF (OPTICALLY-ACTIVE) SULFUR-CONTAINING TRIFUNCTIONAL AMINO-ACIDS BY RADICAL-ADDITION TO (OPTICALLY-ACTIVE) UNSATURATED AMINO-ACIDS [J].

BROXTERMAN, QB ;

KAPTEIN, B ;

KAMPHUIS, J ;

SCHOEMAKER, HE .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6286-6294

[10] TOTAL SYNTHESIS OF (-)-ALPHA-KAINIC ACID [J].

COOPER, J ;

KNIGHT, DW ;

GALLAGHER, PT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05) :553-559

← 1 2 3 4 5 →