Synthesis of (8E,10Z)-tetradeca-8,10-dienal, sex pheromone of horse chestnut leafminer (Cameraria ohridella), and all its geometrical isomers

被引：20

作者：

Hoskovec, M ^{[1
]}

Saman, D ^{[1
]}

Svatos, A ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2000年 / 65卷 / 04期

关键词：

conjugated dienals; stereoselective synthesis; Negishi reaction; sex pheromones; Cameraria ohridella; cross-coupling reactions; alkenes; dienes;

D O I：

10.1135/cccc20000511

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(8E,10Z)-Tetradeca-8,10-dienal (1a), sex pheromone of the horse chestnut leaf miner (Cameraria ohridella; Lepidoptera, Gracillariidae), and its geometrical isomers (1b-1d) were efficiently synthesized using tetrakis(triphenylphosphine)palladium catalyzed cross-coupling reactions of alk-1-ynes or alkenyl alanes with corresponding vinyl iodides. The stereoisomeric purity of obtained tetradecadienals 1a-1d was higher than 95% (GC). Relative electroantennographic (EAG) activities of the prepared compounds la-ld elicited on male antennae supported the previously published identification of the C. ohridella sex pheromone.

引用

页码：511 / 523

页数：13

共 18 条

[1] THE HYDROALUMINATION OF OMEGA-TERBUTOXY ALKYNES - AN EASY ACCESS TO OMEGA-HYDROXY ALKENYL IODIDES - APPLICATION TO THE SYNTHESIS OF DIENIC INSECT PHEROMONES
ALEXAKIS, A
DUFFAULT, JM
[J]. TETRAHEDRON LETTERS, 1988, 29 (48) : 6243 - 6246
[2] MILD PROTECTION AND DEPROTECTION OF ALCOHOLS AS TERT-BUTYL ETHERS IN THE FIELD OF PHEROMONE SYNTHESIS
ALEXAKIS, A
GARDETTE, M
COLIN, S
[J]. TETRAHEDRON LETTERS, 1988, 29 (24) : 2951 - 2954
[3] ANDO T, 1988, AGR BIOL CHEM TOKYO, V52, P1415
[4] COREY EJ, 1975, TETRAHEDRON LETT, P2647
[5] DESCHKA G, 1986, Acta Entomologica Jugoslavica, V22, P11
[6] DIRECT DETERMINATION OF DOUBLE-BOND POSITION IN LONG-CHAIN CONJUGATED DIENES BY T.C4H9+ - CHEMICAL IONIZATION MASS-SPECTROMETRY
EINHORN, J
VIRELIZIER, H
GEMAL, AL
TABET, JC
[J]. TETRAHEDRON LETTERS, 1985, 26 (11) : 1445 - 1448
[7] New potential inhibitors of pheromonal attraction in the oriental fruit moth, Cydia molesta
Hoskovec, M
Hovorka, O
Kalinova, B
Koutek, B
Svatos, A
Saman, D
Vlcek, K
Vrkoc, J
[J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1998, 63 (07) : 1031 - 1044
[8] HOSKOVEC M, CAMERARIA OHRIDELLA
[9] Syntheses of insect sex pheromones. A review of the literature 1990-1998
Koutek, B
Streinz, L
Romanuk, M
[J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1998, 63 (07) : 899 - 954
[10] NEGISHI E, 1988, ORG SYNTH, V66, P60

← 1 2 →