SYNTHESIS OF NATURALLY-OCCURRING 4-ALKYLIDENEGLUTAMIC ACIDS

被引:33
作者
MOODY, CM [1 ]
YOUNG, DW [1 ]
机构
[1] UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
关键词
AMINO ACID; SYNTHESIS; ALKYLIDENEGLUTAMATE; GRIGNARD; NATURAL PRODUCTS;
D O I
10.1016/S0040-4039(00)60652-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enaminone (4), prepared from (2S)-pyroglutamic acid, has been reacted with Grignard reagents to afford a variety of (E)-alkylidene derivatives (8). Three of these have been converted to the 4-alkylideneglutamic acids, (1), (2) and (3), which are identical to known natural products, (2) and (3) being the E-isomers.
引用
收藏
页码:4667 / 4670
页数:4
相关论文
共 24 条
[1]   STEREOSPECIFIC SYNTHESIS OF (2S,4R)-[5,5,5-H-2(3)]-LEUCINE [J].
AUGUST, RA ;
KHAN, JA ;
MOODY, CM ;
YOUNG, DW .
TETRAHEDRON LETTERS, 1992, 33 (32) :4617-4620
[2]   NUCLEOPHILIC RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH WITTIG REAGENTS - AN ENANTIOEFFICIENT SYNTHESIS OF UNSATURATED AMINO-ACIDS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
ROBINSON, NG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) :153-155
[3]  
BENARY E, 1931, CHEM BER, V64, P2543
[4]   GAMMA-METHYLENEGLUTAMIC ACID + RELATED COMPOUNDS FROM PLANTS [J].
BLAKE, J ;
FOWDEN, L .
BIOCHEMICAL JOURNAL, 1964, 92 (01) :136-&
[5]   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
[6]  
BOWLER AN, 1991, THESIS U SUSSEX
[7]   A NEW AMINO-ACID AMIDE IN THE GROUNDNUT PLANT (ARACHIS-HYPOGAEA) - EVIDENCE OF THE OCCURRENCE OF GAMMA-METHYLENEGLUTAMINE AND GAMMA-METHYLENEGLUTAMIC ACID [J].
DONE, J ;
FOWDEN, L .
BIOCHEMICAL JOURNAL, 1952, 51 (04) :451-458
[8]   UNCOMMON AMINO-ACIDS IN SEEDS OF 64 SPECIES OF CAESALPINIEAE [J].
EVANS, CS ;
BELL, EA .
PHYTOCHEMISTRY, 1978, 17 (07) :1127-1129
[9]   ACIDIC AMINO ACIDS OF TULIP - ISOLATION OF GAMMA-ETHYLIDENEGLUTAMIC ACID [J].
FOWDEN, L .
BIOCHEMICAL JOURNAL, 1966, 98 (01) :57-&
[10]   VITAMIN-K-DEPENDENT CARBOXYLATION - INHIBITION BY A PEPTIDE CONTAINING 4-METHYLENE GLUTAMIC-ACID [J].
GUIBE, E ;
DECOTTIGNIESLEMARECHAL, P ;
LEMARECHAL, P ;
AZERAD, R .
FEBS LETTERS, 1984, 177 (02) :265-268