ENANTIOSELECTIVE SYNTHESES OF MONOMORIUM-MINUTUM ANT VENOM ALKALOIDS - (5R)-2-(5-HEXENYL)-5-NONYL-3,4-DIHYDRO-2H-PYRROLE AND (2R,5R)-2-(5-HEXENYL)-5-NONYLPYRROLIDINE FROM (S)-PYROGLUTAMIC ACID

被引：28
作者：
ROSSET, S [1 ]
CELERIER, JP [1 ]
LHOMMET, G [1 ]
机构：
[1] UNIV PARIS 06,CHIM HETEROCYCLES LAB,CNRS,4 PL JUSSIEU,F-75252 PARIS 05,FRANCE
来源：
TETRAHEDRON LETTERS | 1991年 / 32卷 / 51期
关键词：
(S)-PYROGLUTAMIC ACID; CYCLIC IMINE FORMATIONS; CYCLIC IMINE REDUCTIONS;
D O I：
10.1016/0040-4039(91)80523-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe enantioselective syntheses of 2,5-disubstituted pyrroline and pyrrolidine with unsaturated radical, starting from (S)-pyroglutamic acid.
引用
收藏
页码：7521 / 7524
页数：4
相关论文
共 18 条
[1]  
BACKVALL JE, 1990, J ORG CHEM, V55, P826, DOI 10.1021/jo00290a010
[2]   STEREOSELECTIVE SYNTHESIS AND STEREOCHEMICAL DETERMINATION OF 2,5-DIALKLPYRROLIDINES AND 2,6-DIALKYLPIPERIDINES [J].
BACOS, D ;
CELERIER, JP ;
MARX, E ;
ROSSET, S ;
LHOMMET, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (05) :1387-1392
[3]   ANT VENOM ALKALOIDS FROM MONOMORIUM SPECIES - NATURAL INSECTICIDES [J].
BACOS, D ;
BASSELIER, JJ ;
CELERIER, JP ;
LANGE, C ;
MARX, E ;
LHOMMET, G ;
ESCOUBAS, P ;
LEMAIRE, M ;
CLEMENT, JL .
TETRAHEDRON LETTERS, 1988, 29 (25) :3061-3064
[4]  
CASSIER P, 1984, Patent No. 406980
[5]   SYNTHESIS OF (+/-)-TRANS-2,5-DIALKYLPYRROLIDINES FROM THE LUKES-SORM DILACTAM - EFFICIENT PREPARATION OF (+/-)-TRANS-2-BUTYL-5-HEPTYLPYRROLIDINE AND ANALOGS PRESENT IN ANT VENOMS [J].
GESSNER, W ;
TAKAHASHI, K ;
BROSSI, A ;
KOWALSKI, M ;
KALINER, MA .
HELVETICA CHIMICA ACTA, 1987, 70 (08) :2003-2010
[6]   ASYMMETRIC-SYNTHESIS .10. A CHIRAL PYRROLIDINE SYNTHON FOR A NEW APPROACH TO THE SYNTHESIS OF ALKALOIDS [J].
HUANG, PQ ;
ARSENIYADIS, S ;
HUSSON, HP .
TETRAHEDRON LETTERS, 1987, 28 (05) :547-550
[7]   A NEW ROUTE TO OPTICALLY PURE CIS-2,5-DISUBSTITUTED AND TRANS-2,5-DISUBSTITUTED PYRROLIDINES [J].
JEGHAM, S ;
DAS, BC .
TETRAHEDRON LETTERS, 1989, 30 (21) :2801-2804
[8]   NOVEL PYRROLIDINES IN THE VENOM OF THE ANT MONOMORIUM-INDICUM [J].
JONES, TH ;
BLUM, MS ;
ESCOUBAS, P ;
ALI, TMM .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (04) :779-784
[9]   ANALYSIS OF WORKER MONOMORIUM-MINIMUM ANTS VENOM USING GAS-CHROMATOGRAPHY MASS-SPECTROMETRY AND GAS-CHROMATOGRAPHY TANDEM MASS-SPECTROMETRY [J].
LANGE, C ;
CELERIER, JP ;
LHOMMET, G ;
BASSELIER, JJ ;
LEMAIRE, M ;
ESCOUBAS, P ;
CLEMENT, JL .
BIOMEDICAL AND ENVIRONMENTAL MASS SPECTROMETRY, 1989, 18 (09) :780-786
[10]   ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-PYRROLIDINE AND (-)-PYRROLIDINE 197B, A NEW CLASS OF ALKALOID FROM THE DENDROBATID POISON FROG - ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION [J].
MACHINAGA, N ;
KIBAYASHI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1386-1393
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