- SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS
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Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.
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Paragraph 0110
(2018/09/12)
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- SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES
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The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.
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Paragraph 0198; 0199
(2013/09/12)
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- Concise syntheses of insect pheromones using Z-Selective cross metathesis
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Very short synthetic routes to nine cisolefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported (see scheme). These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.
- Herbert, Myles B.,Marx, Vanessa M.,Pederson, Richard L.,Grubbs, Robert H.
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supporting information
p. 310 - 314
(2013/02/23)
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- Facile synthesis of mill moth's sex pheromone components
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An improved method for the preparation of mill moth's sex pheromone components in high diastereomeric purity is described. Copyright Taylor & Francis Group, LLC.
- Hornyanszky, Gabor,Rohaly, Janos,Novak, Lajos
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p. 1533 - 1540
(2008/09/20)
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- Stereodirectional synthesis of the main component of pheromone (9Z,12E)-tetradeca-9,12-dienyl acetate by cross-coupling
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By cross-coupling of alkynyl cuprate with crotyl halides was synthesized (9Z,12E)-tetradeca-9-12-dienyl acetate, the main component of pheromones of several insect species Lepidoptera. The assignment of the chemical shifts of diene system was performed by 1H and 13NMR spectroscopy.
- Matveeva,Erin,Leshcheva,Kurts
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p. 765 - 770
(2007/10/03)
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- SYNTHESIS OF THE SEX PHEROMONE OF THE GRAIN MOTH Ephestia Elutella
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A most convenient synthesis of tetradeca-9Z,12E-dien-1-ol and its acetate - components of the sex pheromone of the grain moth - has been carried out on the basis of a scheme for obtaining a cis-1,trans-4-dienic system.
- Kasymzhanova, M.,Abdukakharov, V. S.,Kamaev, F. G.,Abduvakhabov, A. A.
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p. 708 - 713
(2007/10/02)
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- SYNTHESES WITH SULFONES XLVII : STEREOSELECTIVE ACCESS TO 1,3- AND 1,4-DIENES THROUGH HYDROGENOLYSIS OF BENZENESULFONYLDIENES. APPLICATION TO PHEROMONE SYNTHESIS.
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The stereospecific reduction of EE 2-benzenesulfonyl-1,3-dienes to ZE 1,3-dienes with Grignard reagents under transition metal catalysis is described.Hydrogenolysis of the sulfonyl moiety of 2-benzenesulfonyl-1,4-dienes to ZE 1,4-dienes with sodium dithionite is reported.These techniques have been applied to the stereoselective synthesis of (7E, 9Z) dodecadienyl acetate 3d, (9Z, 11E) tetradecadienyl acetate 3e and (9Z, 12E) tetradecadienyl acetate, 6b.
- Cuvigny, T.,Penhoat, C. Herve Du,Julia, M.
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p. 859 - 872
(2007/10/02)
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- Pheromones, XXXV. - Stereoselective Syntheses of 1,4-Alkadienes
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The stereoselective synthesis of 1,4-alkadienes via Julia synthesis, Wittig reaction, Crombie synthesis and methylene interruption of conjugated alkadienylphosphonates is described.
- Bestmann, Hans Juergen,Koschatzky, Karl-Heinrich,Plenchette, Alain,Suess, Joachim,Vostrowsky, Otto
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p. 536 - 544
(2007/10/02)
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