34010-15-6Relevant articles and documents
SYNTHESIS OF STRAIGHT-CHAIN LEPIDOPTERAN PHEROMONES THROUGH ONE- OR TWO- CARBON HOMOLOGATION OF FATTY ALKENES
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, (2020/02/14)
Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.
Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones
Zubrytski,Kananovich,Matiushenkov
, p. 813 - 823 (2017/08/02)
Oxidative cleavage of exo- and endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl acetate (European oak leafroller Tortrix viridana), and (3E,8Z,11Z)-tetradeca-3,8,11-trien-1-yl acetate (tomato leafminer Tuta absoluta).
SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES
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Paragraph 0189; 0190, (2013/09/12)
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.
Concise syntheses of insect pheromones using Z-Selective cross metathesis
Herbert, Myles B.,Marx, Vanessa M.,Pederson, Richard L.,Grubbs, Robert H.
supporting information, p. 310 - 314 (2013/02/23)
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.
Remarkable regioselective hydroboration of terminal alkenes by calcium borohydride
Narasimhan,Prasad, K. Ganeshwar,Madhavan
, p. 1141 - 1144 (2007/10/02)
Calcium borohydride is found to hydroborate unsaturated systems in the presence of ethyl acetate. The reaction exhibits remarkable selectivity towards terminal double bonds. Several Z-11-alken-1-ol pheromones are synthesized using this method.
SYNTHESIS OF PHEROMONES, IV. CHEMISTRY OF THE WITTIG REACTION, I. EFFECTS OF REACTION CONDITIONS ON THE STEREOSELECTIVITY AND YIELD OF THE WITTIG REACTION
Vinczer, Peter,Juvancz, Zoltan,Novak, Lajos,Szantay, Csaba
, p. 797 - 820 (2007/10/02)
The reactions of nonstabilized triphenylphosphorus ylides with aldehydes have been studied in detail.The stereochemistry and yields of the alkene products are highly dependent upon base used for the generation of the ylide, the solvent and reaction temperature.The synthesis of sex pheromone components by Wittig reaction are also described.
SYNTHESIS OF (Z)-TETRADEC-11-EN-1-OL AND (Z)-HEXADEC-11-EN-1-OL FROM DODECANE-1,12-DIOL
Zakharkin, L. I.,Guseva, V. V.
, p. 733 - 736 (2007/10/02)
A method have been developed for obtaining (Z)-tetradec-11-en-1-ol and (Z)-hexadec-11-en-1-ol via dodec-11-yn-1-ol.
INSECT SEX PHEROMONES. STEREOSELECTIVE SYNTHESIS OF SEVERAL (Z)- AND (E)-ALKEN-1-OLS, THEIR ACETATES, AND OF (9Z,12E)-9,12-TETRADECADIEN-1-YL ACETATE
Rossi, Renzo,Carpita, Adriano,Gaudenzi, Loretta,Quirici, Maria Grazia
, p. 237 - 246 (2007/10/02)
Several female sex pheromone components produced by moths belonging to the order of Lepidoptera, and potential attractants of Dacus oleae (Diptera:Tripetidae) have been synthesized in high chemical and stereoisomeric purity by improved acetylenic routes involving alkylation of lithium 1-alkyn-1-ides in HMPT, followed by (Z) and (E) highly stereoselective reduction of the derived internal alkynes.Particular care has been paid to optimize the parameters of the reactions used and to evaluate the chemical and isomeric purity of the reaction products.The compounds synthesized include (Z)- and (E)-5-nonen-1-ol, (Z)- and (E)-7-dodecen-1-yl acetate, (Z)- and (E)-7-teradecen-1-yl acetate, (Z)- and (E)-7-nonen-1-ol, (Z)- and (E)-9-tetradecen-1-yl acetate, (Z)- and (E)-10-tetradecen-1-yl acetate, (Z)- and (E)-11-tetradecen-1-yl acetate.Pure (Z)-6-nonen-1-ol, which is an attractant of olive fruit fly, D. oleae, and very probably, a constituent of the sex pheromone of females of this insect, has been prepared by a rather efficient copper-catalyzed reaction between (Z)-3-hexen-1-ylmagnesium bromide and oxetane. (9Z,12E)-9,12-Tetradecadien-1-yl acetate, which is the pheromone of Anagasta kuenniella, Ephestia elutella, Cadra figulella, Spodoptera exigua, S. litura, and a component of the sex pheromones of several other Lepidoptera, has been conveniently prepared by using the copper-catalyzed coupling reaction between (E)-1-chloro-2-butene and 10-tetrahydropyranyloxy-1-decenylmagnesium bromide, followed by acetylation and Z-stereoselective reduction of the derived 1,4-enyne.All syntheses have been conducted on a scale to yield less than 50 mmol of the pure sex pheromone components, but seem adaptable for much larger quantities.
