Asymmetric total synthesis of syringolide 1, a nonproteinaceous elicitor

被引:20
作者
Ishihara, J [1 ]
Sugimoto, T [1 ]
Murai, A [1 ]
机构
[1] HOKKAIDO UNIV,GRAD SCH SCI,DIV CHEM,SAPPORO,HOKKAIDO 060,JAPAN
关键词
D O I
10.1016/S0040-4020(97)10062-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An asymmetric synthesis of syringolide 1, one of the elicitors produced by Pseudomonas syringae pv. tomato, is described. It was synthesized from 2-(1-oxoethyl)-2-buten-4-olide via 1,4-addition of alkenyl cuprate, asymmetric dihydroxylation, and intramoleculr Michael reaction. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:16029 / 16040
页数:12
相关论文
共 17 条
[1]   TETRAFLUOROSILANE IS A MILD AND VERY SELECTIVE REAGENT FOR THE CLEAVAGE OF SILYL-PROTECTED ALCOHOLS [J].
COREY, EJ ;
YI, KY .
TETRAHEDRON LETTERS, 1992, 33 (17) :2289-2290
[2]   TOBACCO MOSAIC-VIRUS ELICITOR COAT PROTEIN GENES PRODUCE A HYPERSENSITIVE PHENOTYPE IN TRANSGENIC NICOTIANA-SYLVESTRIS PLANTS [J].
CULVER, JN ;
DAWSON, WO .
MOLECULAR PLANT-MICROBE INTERACTIONS, 1991, 4 (05) :458-463
[3]   Biomimetic synthesis of the microbial elicitor syringolide 2 [J].
Henschke, JP ;
Rickards, RW .
TETRAHEDRON LETTERS, 1996, 37 (20) :3557-3560
[4]   Enantioselective syntheses of syributin 1 and novel C-glycosidic elicitors syringolides 1 and 2 [J].
Honda, T ;
Mizutani, H ;
Kanai, K .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9374-9378
[5]   A SYNTHESIS OF PILOCARPINE [J].
HORNE, DA ;
FUGMANN, B ;
YAKUSHIJIN, K ;
BUCHI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :62-64
[6]  
Ishihara J, 1996, SYNLETT, P335
[7]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[8]   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
[9]   SYNTHESIS OF (-)-SYRINGOLIDE-1 AND (-)-SYRINGOLIDE-2 [J].
KUWAHARA, S ;
MORIGUCHI, M ;
MIYAGAWA, K ;
KONNO, M ;
KODAMA, O .
TETRAHEDRON, 1995, 51 (32) :8809-8814
[10]   REACTIONS INVOLVING SELENIUM METAL AS AN ELECTROPHILE .2. A GENERAL PROCEDURE FOR THE PREPARATION OF UNSATURATED BETA-DICARBONYL COMPOUNDS [J].
LIOTTA, D ;
SAINDANE, M ;
BARNUM, C ;
ENSLEY, H ;
BALAKRISHNAN, P .
TETRAHEDRON LETTERS, 1981, 22 (32) :3043-3046