ALBERT

All Library Books, journals and Electronic Records Telegrafenberg

X
feed icon rss

Your email was sent successfully. Check your inbox.

An error occurred while sending the email. Please try again.

Proceed reservation?

Export
Filter
  • Articles  (5)
  • sex pheromone  (3)
  • Asymmetric synthesis
  • 1995-1999  (5)
  • 1997  (5)
  • 1
    Electronic Resource
    Electronic Resource
    (Z)6, (E)8-Heneicosadien-11-One: Synergistic Sex Pheromone Component of Douglas-Fir Tussock Moth, Orgyia pseudotsugata (McDunnough) (Lepidoptera: Lymantriidae) (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 19-34 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Lymantriidae ; Orgyia pseudotsugata ; tussock moth ; (Z)6,(Z)9-heneicosadien-11-one ; (Z)6,(E)8-heneicosadien-11-one ; (Z)6,(Z)9-heneicosadien-11-one ; sex pheromone ; synergism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Three candidate sex pheromone components, (Z)6,(Z)9-, (Z)6,(E)8-, and (Z)6,(E)9-heneicosadien-11-one (Z6Z9, Z6E8, and Z6E9) were identified in pheromone gland extracts of female Douglas-fir tussock moths (DFTM), Orgyia pseudotsugata (McDunnough). Their occurrence in subnanogram quantities in extracts and structural conversion during analytical procedures and bioassays complicated chemical identifications. Complete identification required comparative analyses of stereoselectively synthesized and female-produced dienones by coupled gas chromatographic–electroantennographic detection (GC-EAD), high-performance liquid chromatography (HPLC) and coupled GC–mass spectrometry (MS). Determination of the pheromone component was contingent upon an experimental design that minimized structural rearrangement of dienones before and during the field test. In a 40-min field experiment, acetonitrile solutions of each of the above dienones were carried on Dry Ice to traps and were syringed onto cotton release devices below trap lids. In combination with the previously known sex pheromone component of DFTM, (Z)6-heneicosen-11-one (Z6), Z6E8 was the only synergistic dienone and the mixture was highly attractive. Because Z6 by itself attracts seven species of tussock moths (two sympatric with DFTM), a blend of Z6 and Z6E8 may impart specificity to DFTM pheromone communication. In commercial lures, this binary blend may facilitate species-specific, sensitive monitoring and efficacious control by mating disruption of this important forest defoliator.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/B:JOEC.0000006343.38471.c7
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 2
    Electronic Resource
    Electronic Resource
    Sex Pheromone Components of the Apple Leafminer, Lyonetia prunifoliella (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1119-1130 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Lyonetiidae ; Lyonetia prunifoliella ; Perileucoptera coffeella ; Lyonetia clerkella ; Leucoptera malifoliella ; sex pheromone ; synergism ; 10,14-dimethyloctadec-1-ene ; 5,9-dimethyloctadecane ; 5,9-dimethylheptadecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Three methylated hydrocarbons, 10,14-dimethyloctadec-1-ene (10Me14Me-1-ene-18Hy = 5Me9Me-17-ene-18Hy), 5,9-dimethyloctadecane (5Me9Me-18Hy), and 5,9-dimethylheptadecane (5Me9Me-17Hy), are synergistic sex pheromone components of the leafminer Lyonetia prunifoliella. Compounds extracted from female pheromone glands were identified by coupled gas chromatographic–electroantennographic detection (GC-EAD), and one compound, 10Me14Me-1-ene-18Hy, also by coupled GC–mass spectrometry. In field trapping experiments, 10Me14Me-1-ene-18Hy, 5Me9Me-18Hy, and 5Me9Me-17Hy singly were unattractive to males but in ternary combination attracted numerous male moths. Attractiveness of the three-component blend significantly exceeded that of two-component blends. No attraction of males to pheromone lures without 10Me14Me-1-ene-18Hy indicates that this compound is essential for pheromone communication of L. prunifoliella. Common C-5 and C-9 methyl branches in lyonetiid pheromone hydrocarbons suggest a common biosynthetic pathway; the presence of 5Me9Me-17Hy and 5Me9Me-18Hy in pheromone blends of L. prunifoliella and Leucoptera malifoliella provides evidence for phylogeny of lyonetiid chemical communication. Determination of the stereoisomeric composition is required to completely describe the pheromone blend of L. prunifoliella and to support the hypothesis of phylogenetically related sex pheromones.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/B:JOEC.0000006390.43868.3b
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 3
    Electronic Resource
    Electronic Resource
    Identification of Sex Pheromone Components of Nettle Caterpillar, Setothosea asigna (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 2187-2196 
    Details
    ISSN: 1573-1561
    Keywords: Setothosea asigna ; nettle caterpillar ; Limacodidae ; Lepidoptera ; sex pheromone ; (E)-9-dodecenal ; (E)-9,11-dodecadienal ; oil palm ; Elaeis guineensis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Gas chromatographic–electroantennographic detection (GC-EAD) analyses of female nettle caterpillar, Setothosea asigna, pheromone gland extracts revealed seven antennally active compounds. Based on their retention indices on three fused silica columns (DB-5, DB-23, and DB-210), these compounds were hypothesized and, through comparative GC, GC-EAD and GC-mass spectrometry with authentic standards, confirmed to be Δ10-undecenal, dodecanal, (E)-9-dodecenal (E9–12:Ald), (Z)-9-dodecenal, (E)-9-dodecen-1-ol, (E)-9,11-dodecadienal (E9,11–12:Ald), and (E)-9,11-dodecadienol. E9–12:Ald and E9,11–12:Ald were most abundant in female S. asigna pheromone extracts. In field trapping experiments in Palembang, Indonesia, synthetic E9–12: Ald and E9,11–12:Ald at a 1:1 ratio, but not singly, attracted S. asigna males. Attractiveness of these two aldehydes could not be enhanced further through the addition of their corresponding alcohols and/or other aldehydic candidate pheromone components. Use of E9–12:Ald and E9,11–12:Ald for pheromone-based monitoring of S. asigna populations will require lure formulations that minimize pheromone degradation by ultraviolet radiation and atmospheric oxidation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/B:JOEC.0000006438.03728.1a
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 4
    Electronic Resource
    Electronic Resource
    Enantioselective synthesis of α-phosphanyl ketones and 2-phosphanyl alcoholsDedicated to Professor Hans Paulsen on the occasion of his 75th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 345-363 
    Details
    ISSN: 0947-3440
    Keywords: α-Phosphanyl ketones ; 2-Phosphanyl alcohols ; α-Phosphanyl hydrazones ; Asymmetric α-phosphanylation ; Phosphane-borane adducts ; Asymmetric synthesis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An efficient, highly enantioselective methodology for the synthesis of α-phosphanyl ketones 7 and 2-phosphanyl alcohols 12 and 13, important hemilable ligands for enantioselective homogeneous catalysis and chiral building blocks in general, has been developed. The key step of this first enantio-selective synthesis of α-phosphanyl ketones is the diastereo-selective phosphanylation of SAMP hydrazones 2 to produce α-phosphanyl hydrazones, isolated as the more stable borane adducts 6. Subsequent ozonolysis afforded α-phosphanyl ketones 7. The enantioselective synthesis of 2-phosphanyl alcohols 12 and 13 has been accomplished by two fundamentally different procedures: the phosphanylation of unsubstituted chiral aldehyde hydrazones 9 and the alkylation of α-diphenylphopshanyl acetaldehyde SAMP hydrazone 10. After separation of the minor diastereomer, the borane-protected α-phosphanyl aldehyde hydrazones 11 were converted to unprotected 2-phosphanyl alcohols 13 by ozonolysis, reduction and removal of the borane group. The absolute configuration of the functionalized phosphanes was determined by X-ray analysis, NOE experiments or polarimetry.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970212
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 5
    Electronic Resource
    Electronic Resource
    Total Synthesis of (+)-3-Oxacarbacyclin 1. Retrosynthesis and Asymmetric Olefination through Horner-Wadsworth-Emmons, Peterson and Martin ReactionsDedicated to Prof. Dr. Klaus Hafner on the occasion of his 70th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 2419-2431 
    Details
    ISSN: 0947-3440
    Keywords: (+)-3-Oxacarbacyclin ; Asymmetric synthesis ; Horner-Wadsworth-Emmons reaction ; Peterson reaction ; Martin reaction ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The asymmetric Horner-Wadsworth-Emmons (HWE) reaction of the prochiral ketones 8a/b with the phosphonoacetates 10a, ent-10a, 10b and rac-16, which contain 8-phenylmenthol, 8-phenylnormenthol and trans-2-(triphenylsilyl)-cyclohexanol, respectively, as chiral auxiliaries, were studied. The HWE reaction of 8a with the phosphonoenolates Li-10a/b at low temperatures gave the esters 7a/b and 11a/b in high yields with diastereoselectivities up to 97:3. The (E)-configured esters 7a/b serve as starting material for the total synthesis of (+)-3-oxacarbacyclin. Similarly, the reaction of 8b with ent-Li-10a gave the esters ent-7b and ent-11b in a ratio of 95:5 in 82% yield. The olefination of 8b with rac-16 afforded a mixture of the esters rac-17 and rac-18, of yet unassigned configuration, in a ratio of 70:30. The HWE reactions of 8a/b with Li-10a, ent-Li-10a and rac-Li-10b show linear temperature-diastereoselectivity relationships. The stereochemical course of the HWE reactions can be understood in terms of a selective addition of the chiral (E)-configured phosphonoenolate from its least hindered side to the ketone 8 at the convex side. The asymmetric Peterson reaction of 8b with the silyl enolate Li-20 gave the esters ent-7b and ent-11b in a ratio of 89:11. The diastereomerically pure β-hydroxy esters 22, rac-25 and 27, which contain 8-phenyl-menthol, trans-2-(triphenylsilyl)cyclohexanol and 3-{[(3,5-dimethylphenyl)phenylsulfonyl]amino}isoborneol, respectively, as chiral auxiliaries, were prepared by a highly selective addition of the enolates Li-21, rac-Li-24 and Li-26 to the ketone 8b. The asymmetric Martin dehydration of 22, rac-25 and 27 with the sulfurane 23 proceeds with stereoselectivities ranging from 82:18 to 99:1. Interestingly, the HWE, Peterson and Martin reactions involving 8-phenylmenthol as the chiral auxiliary all proceed with the same sense of asymmetric induction.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719971205
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
Close ⊗
This website uses cookies and the analysis tool Matomo. More information can be found here...