- Improved Synthesis of (3E,6Z,9Z)-1,3,6,9-Nonadecatetraene, Attraction Inhibitor of Bruce Spanworm, Operophtera bruceata, to Pheromone Traps for Monitoring Winter Moth, Operophtera brumata
-
The winter moth, Operophtera brumata (Lepidoptera: Geometridae), is an early-season defoliator that attacks a wide variety of hardwoods and, in some cases, conifers. The insect is native to Europe but has become established in at least three areas of Nort
- Khrimian, Ashot,Lance, David R.,Mastro, Victor C.,Elkinton, Joseph S.
-
experimental part
p. 1828 - 1833
(2010/08/19)
-
- Highly efficient one-pot double-Wittig approach to unsymmetrical (1Z,4Z,7Z)-homoconjugated trienes
-
We describe a novel one-pot double-Wittig approach towards unsymmetrically substituted skipped trienes using the symmetrical (Z)-hex-3- ene-1,6-bis(triphenylphosphonium iodide) (2) as key reagent. Double alkenylation of the corresponding bis(ylide) 3 with sequentially added aldehydes gives (Z)-1,4,7-homoconjugated trienes in good yields. Dissymmetrization of the bis(ylide) 3 is feasible, since it displays enhanced reactivity compared to the monoylide resulting from the first olefination. Symmetrical products from statistical coupling of the bis(ylide) 3 can be drastically suppressed by slow release of the first aldehyde component through in situ thermal decomposition of an intermediate aluminate complex, generated by reduction of a methyl ester with DIBAL-H. The novel strategy is successfully applied to the one-pot synthesis of functionalized and isotopically labelled polyunsaturated fatty acids as well as to the synthesis of the geometrid moth pheromone (3Z,6Z,9Z)-nonadeca-1,3,6,9-tetraene (6a). The dissymmetrization strategy was also found to be suitable for the synthesis of homoconjugated dienes from 1,3-propylbis(triphenylphosphonium bromide).
- Pohnert, Georg,Boland, Wilhelm
-
p. 1821 - 1826
(2007/10/03)
-
- SYNTHETIC STUDIES IN THE FIELD OF ATTRACTIVE SUBSTANCES (SEX ATTRACTANTS) OF INSECTS. SYNTHESIS OF NONADECA-1,cis-3,cis-6,cis-9-TETRAENE - THE SEX PHEROMONE OF Operophtera brumata (LEPIDOPTERA; GEOMETRIDAE)
-
A new synthesis of nonadeca-1,cis-3,cis-6,cis-9-tetraene, the sex pheromone of the winter moth Operophtera brumata, has been developed which involves the alkylation of bromomagnesium derivatives of tetrahydropyranyl ethers of mono- and diacetylenic alcohols by a monoacetylenic bromide, followed by hydrogenation of the resulting triynol to a trienol, oxidation of the latter to an aldehyde, and interaction of the latter with methylenetriphenylphosphorane.
- Nikolaeva, L. A.,Kovalev, B. G.,Ishchenko, R. I.
-
p. 103 - 105
(2007/10/02)
-
- C3-homologation. Synthesis of C19-skipped polyenic pheromones
-
Total synthesis of three sex pheromone components including an all-cis diene or triene unit are described. Starting from decanal, cis-Wittig reactions, by using C3 homologating agent 4 and convenient phosphonium salts, allowed us to built up all-cis skipp
- Viala,Munier,Santelli
-
p. 3347 - 3352
(2007/10/02)
-
- Pheromones, 57.- Synthesis of Lepidoptera Polyene Pheromones and of Structural Analogs.- Acetylenic Synthesis, Wittig Olefination, and Kolbe Electrolysis
-
By a combination of acetylenic syntheses with Wittig olefination as well as by mixed Kolbe electrolysis alkadienes, alkatrienes, and alkatetraenes (sex attractants of Lepidoptera and structural analogs)were synthesized.
- Bestmann, Hans Juergen,Roth, Kurt,Michaelis, Karl,Vostrowsky, Otto,Schaefer, Hans J.,Michaelis, Ralf
-
p. 417 - 422
(2007/10/02)
-
- Short synthesis of 1,3Z,6Z,9Z-tetraene hydrocarbons. Lepidopteran sex attractants
-
A short, convergent synthesis of 1,3Z,6Z,9Z-tetraene hydrocarbons was developed.A key step was the regioselective alkylation of 1,5-dibromo-2-pentyne.The method was used to synthesize tetraenes of chain lengths C18-C20, to be used in field trials as sex attractants and (or) inhibitors of the winter moth, Operophtera brumata L., and the Bruce spanworm O. bruceata H. (Lepidoptera: Geometridae).
- Millar, Jocelyn G.,Underhill, Edward W.
-
p. 2427 - 2430
(2007/10/02)
-
- PHEROMONE-XLII. 1,3,6,9-NONADECATETRAEN, DAS SEXUALPHEROMON DES FROSTSPANNERS OPEROPHTERA BRUMATA (GEOMETRIDAE).
-
By means of GC and GCMS analysis and electrophysiological investigations (Z3,Z6,Z9)-1,3,6,9-nonadecatetraene was identified as sex pheromone of the winter moth O.Brumata, and prepared by stereoselective synthesis methods.
- Bestmann, Hans Juergen,Brosche, Thorolf,Koschatzky, Karl Heinrich,Michaelis, Karl,Platz, Hans,et al.
-
p. 4007 - 4010
(2007/10/02)
-