SYNTHESIS OF (-)-SYRINGOLIDE-1 AND (-)-SYRINGOLIDE-2

被引:30
作者
KUWAHARA, S
MORIGUCHI, M
MIYAGAWA, K
KONNO, M
KODAMA, O
机构
[1] Laboratory of Agricultural Chemicals, Faculty of Agriculture, Ibaraki University, Inashiki-gun, Ibaraki, 300-03, Ami-machi
关键词
D O I
10.1016/0040-4020(95)00488-T
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective synthesis of (-)-syringolides 1 and 2 which were isolated as specific elicitors produced by Pseudomonas syringae pv, tomato was accomplished in 11 steps from diethyl D-tartrate. The specific rotations of synthetic samples were in good accord with those of the natural syringolides, and synthetic syringolide 2 showed almost the same biological activity as that of natural syringolide 2.
引用
收藏
页码:8809 / 8814
页数:6
相关论文
共 10 条
[1]   RPS2 OF ARABIDOPSIS-THALIANA - A LEUCINE-RICH REPEAT CLASS OF PLANT-DISEASE RESISTANCE GENES [J].
BENT, AF ;
KUNKEL, BN ;
DAHLBECK, D ;
BROWN, KL ;
SCHMIDT, R ;
GIRAUDAT, J ;
LEUNG, J ;
STASKAWICZ, BJ .
SCIENCE, 1994, 265 (5180) :1856-1860
[2]   AMPLIFICATION OF CYANIDE ION PRODUCTION BY MICELLAR REACTION OF KETO OXIMES WITH PHOSPHONOFLUORIDATES AND PHOSPHOROFLUORIDATES [J].
EPSTEIN, J ;
CANNON, P ;
SWIDLER, R ;
BARAZE, A .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) :759-762
[3]   ALKYLATION OF DIANIONS OF BETA-KETO-ESTERS [J].
HUCKIN, SN ;
WEILER, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) :1082-1087
[4]   HIGHLY SELECTIVE TOTAL SYNTHESIS OF ENANTIOMERICALLY PURE (-)-ANISOMYCIN [J].
IIDA, H ;
YAMAZAKI, N ;
KIBAYASHI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) :1069-1073
[5]   SYNTHESIS AND ABSOLUTE-CONFIGURATION OF SYRINGOLIDE 2, AN ELICITOR FROM PSEUDOMONAS-SYRINGAE PV TOMATO [J].
KUWAHARA, S ;
MORIGUCHI, M ;
MIYAGAWA, K ;
KONNO, M ;
KODAMA, O .
TETRAHEDRON LETTERS, 1995, 36 (18) :3201-3202
[6]   A CONVENIENT PROCEDURE FOR THE MONOSILYLATION OF SYMMETRICAL 1,N-DIOLS [J].
MCDOUGAL, PG ;
RICO, JG ;
OH, YI ;
CONDON, BD .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (17) :3388-3390
[7]   THE STRUCTURES OF SYRINGOLIDE-1 AND SYRINGOLIDE-2, NOVEL C-GLYCOSIDIC ELICITORS FROM PSEUDOMONAS-SYRINGAE PV TOMATO [J].
MIDLAND, SL ;
KEEN, NT ;
SIMS, JJ ;
MIDLAND, MM ;
STAYTON, MM ;
BURTON, V ;
SMITH, MJ ;
MAZZOLA, EP ;
GRAHAM, KJ ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :2940-2945
[8]   THE SYRINGOLIDES - BACTERIAL C-GLYCOSYL LIPIDS THAT TRIGGER PLANT-DISEASE RESISTANCE [J].
SMITH, MJ ;
MAZZOLA, EP ;
SIMS, JJ ;
MIDLAND, SL ;
KEEN, NT ;
BURTON, V ;
STAYTON, MM .
TETRAHEDRON LETTERS, 1993, 34 (02) :223-226
[9]   STANNYLATION-DESTANNYLATION - PREPARATION OF ALPHA-ALKOXY ORGANOLITHIUM REAGENTS AND SYNTHESIS OF DENDROLASIN VIA A CARBINYL CARBANION EQUIVALENT [J].
STILL, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (05) :1481-1487
[10]   TOTAL SYNTHESES OF (+)-SYRINGOLIDES-1-AND-2 AND (-)-SYRINGOLIDES-1-AND-2 [J].
WOOD, JL ;
JEONG, S ;
SALCEDO, A ;
JENKINS, J .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) :286-287