- INSECT PHEROMONES AND THEIR ANALOGS. IV. THE SYNTHESIS OF THE SEX ATTRACTANT OF THE HONEY BEE Apis mellifera
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A new and convenient method for the synthesis of 9-oxodec-2E-enoic acid (I) from the readily accessible octa-2E,7-dienyl acetate is proposed.From the latter compound by a series of transformations (oxidation of the terminal double bond to a ketone, saponification, hydrogenation, and oxidation with Corey's reagent) 7-oxooctanal is obtained, and this is condensed by the Knoevenagel reaction with malonic acid to give compound (I) with a yield of 69percent.
- Dzhemilev, U. M.,Balezina, G. G.,Tolstikov, G. A.
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- New approach to the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee, from the telomer of butadiene and water
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A new approach was proposed for the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee (Apis mellifera L.), starting from the available telomer of butadiene and water (2E,7-octadien-1-ol) using in the key steps partial ozonolysis of the corresponding carbonyl compound, selective oxidation of the conjugated aldehyde into a carboxylic acid, and alkylation of acetoacetic ester to introduce the oxo group.
- Ishmuratov,Vydrina,Nasibullina,Yakovleva,Muslukhov,Tolstikov
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- A two-step synthesis of the 'Queen substance' of the honey bee
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A synthesis of the 'queen substance' was accomplished in two steps from readily available starting materials. The key step was a novel one-pot reduction of 7-oxooctanoic acid to 7-oxooctanal followed by condensation with malonic acid.
- Ebert
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- INSECT PHEROMONES AND THEIR ANALOGS. XV. THE SYNTHESIS OF 9-OXODEC-2E-ENOIC ACID - A PHEROMONE OF THE HONEYBEE Apis melliferana
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A new effective route to the synthesis of 7-oxooctanal has been found which is based on the ozonolysis of the tetrahydropyran-2-yl ether of 7-methyloct-7-en-1-ol - the product of the coupling of the readily available methallyl chloride and the Grignard reagent from the corresponding ether of 5-bromopentan-1-ol.From the 7-oxooctanal has been obtained 9-oxodec-2E-enoic acid - a pheromone of the honeybee Apis melliferana.
- Odinokov, V. N.,Ishmuratov, G. Yu.,Ladenkova, I. M.,Tolstikov, G. A.
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- Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera
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Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the γ-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera.
- Olszewski, Tomasz K.,Bomont, Catherine,Coutrot, Philippe,Grison, Claude
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supporting information; experimental part
p. 2354 - 2358
(2010/10/19)
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- Practical synthesis of (E)-α,β-unsaturated carboxylic acids using a one-pot hydroformylation/decarboxylative Knoevenagel reaction sequence
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Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, one-pot procedure for the synthesis of (E)-α,β-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-α,β-unsaturated carboxylic acids in good yields and with excellent regio-and stereocontrol. The practicability of this process has been demonstrated by a short protecting group-free synthesis of the queen honeybee pheromones 9-ODA[( E)-9-oxodec-2-enoic acid] and 9-HDA[( E)-9-hydroxydec-2-enoic acid].
- Kemme, Susanne T.,?mejkal, Tomá?,Breita, Bernhard
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supporting information; experimental part
p. 989 - 994
(2009/05/27)
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- Synthesis of a multifunctional pheromone of the honeybee Apis mellifera via condensation of 7-oxooctanal with malonic acid
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Condensation of 7-oxooctanal with malonic acid in a Doebner reaction produces 9-oxo-2E-decenoic acid (42% yield) and a comparable amount of products from Tishchenko disproportionation of the starting aldehyde (7-oxooctyl-7- oxooctanoate) and re-esterification by acetic acid (7-oxooct-1-ylacetate and 7-oxooctanoic acid).
- Ishmuratov,Yakovleva,Botsman,Ishmuratova,Muslukhov,Khambalova,Tolstikov
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- Composition, method, and apparatus to attract bees
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Applicant's invention includes an improved bee attracting composition. Applicant's invention further includes a bee attracting device formed from his improved bee attracting composition. Applicant's bee attracting device can be further coated with a second bee attracting composition. Applicant's invention further includes a method and apparatus for attracting and immobilizing bees using a substrate coated with an adhesive composition upon which Applicant's bee attracting composition is disposed.
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- Synthesis of 10-hydroxy- and 9-oxo-2E-decenoic acids from oleic acid
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A practical synthesis of biologically active 10-hydroxy- and 9-oxo-2E-decenoic acids, components of mandibular gland secretion of honeybee (Apis mellifera L.), is developed using ozonolysis - reduction of oleic acid and 1,9-diacetoxynon-1-ene in the key steps.
- Kharisov,Botsman,Botsman,Ishmuratova,Ishmuratov,Tolstikov
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p. 145 - 148
(2007/10/03)
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- Tungsten(0) alkylidene complexes stabilized as pyridinium ylides: New aspects of their synthesis and reactivity
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The interaction of dihydropyridines with alkoxycarbene complexes of tungsten has been shown to lead to pyridinium ylid complexes: this transformation has now been applied to the synthesis of a hydroxyl-containing ylid complex by ring-opening of the pentacarbonyl (2-oxacyclopentylidene) tungsten(0) complex and to the synthesis of a series of chiral ylid complexes both from chiral and non-chiral carbene complexes by the use of dihydropyridines and dihydronicotines, respectively. The transfer of the alkylidene moiety of these complexes to nucleophilic olefins will be outlined and discussed. Especially relevant is the interaction of these pyridinium ylid complexes with unsaturated substrates such as dihydropyridines, enamines, and β-alkoxy bis(trimethyl-silyl) ketene acetals. This latter reaction leads to conjugated carboxylic acids, and has been be applied to a new synthesis of a honey bee pheromone, the queen substance.
- Rudler, Henri,Durand-Réville, Thomas
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p. 571 - 587
(2007/10/03)
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- A simple and facile microwave assisted synthesis of 9-oxo-2(E)-decenoic acid
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Synthesis of 9-oxo-2(E)-decenoic acid 1, the queen bee substance of Apis Mellifera, is reported utilizing microwave radiation in assisting the alkylation / decarboxylation and Knoevenagel condensation reactions.
- Kad,Kaur,Nayyar,Kaur,Singh
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p. 715 - 716
(2007/10/03)
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- Aleuritic acid in the preparation of (Z)-9-octadecene-1,18-dioic acid (intermediate in civetone synthesis) and queen substance of honey-bee utilizing phosphonate carbanions
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Wittig-Horner-Emmons olefination on aldehydes derived from aleuritic acid leading to the formation of both pure Z and E isomers of 9-octadecene-1,18 dioic acid, in good yield (valuable intermediate for musk perfume civetone) and a synthesis of 9-oxo-(E)-2-decenoic acid (queen bee substance) are reported.
- Subramanian,Ahuja, Seema
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p. 1043 - 1046
(2007/10/03)
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- Synthesis of (E)-9-oxo-2-decenoic acid and (E)-10-hydroxy-2-decenoic acid
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Syntheses of (E)-9-oxo-decenoic acid (III), queen's substance and (E)-10-hydroxy-2-decenoic acid (V), a componenet of royal jelly and a bee pheromone, have been accomplished through a common intermediate (I).
- Trehen, I R,Vig, Rakesh,Singh, Vasundhara,Sharma, Sushma,Kad, G L
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p. 257 - 259
(2007/10/02)
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- Total synthesis of queen substance of honeybee using an organosilicon route
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O-silylated enolates are used as the key intermediates in the total synthesis of queen substance. The synthesis proceeds in 7 steps and affords the desired pheromone with very high stereoselectivity and 34% overall yield.
- Bellassoued,Majidi
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p. 7253 - 7254
(2007/10/02)
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- NEW PREPARATION OF α,β-UNSATURATED ESTERS FROM 1-ALKENES VIA TWO CARBON HOMOLOGATION ROUTE. SYNTHESIS OF QUEEN SUBSTANCE
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2-Methylthio-4-alkenoic esters prepared from 1-alkenes and ethyl methylsulfinylacetate are converted into α,β-unsaturated esters via hydrogenation, oxidation, and thermolysis.This method was applied to the synthesis of queen substance.
- Ishibashi, Hiroyuki,Ohnishi, Minako,Senda, Toshihiko,Ikeda, Masazumi
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p. 857 - 864
(2007/10/02)
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- Cumulated Ylides XIX. Chain-lenghthening Difunctionalization of Grignard Compounds by Reaction with Ketenylidenetriphenylphosphorane. A New Route to (E)-α,β-Unsaturated Ketones and the Queen Substance
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The reaction of Grignard compounds with ketenylidenetriphenylphosphorane and subsequent hydrolysis yields 2-oxoalkylidenetriphenylphosphoranes.The latter undergo Wittig reaction, whereby (E)-α,β-unsaturated ketones are obtained.An application of this strategy to the synthesis of carbonyl homologues of Lepidoptera pheromones and the queen substance is shown.
- Bestmann, Hans Juergen,Schmidt, Martin,Schobert, Rainer
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- SYNTHESIS OF QUEEN SUBSTANCE VIA THREE CARBON HOMOLOGATION ROUTE
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The acetoxyaldehyde 9 prepared in five steps from methylcyclohexene 4 furnished the alkylidine succinic ester 12 when reacted with diethyl diethoxyphosphinylbutanedioate 11.The ester 12 was transformed to the half ester 17, which on oxidative decarboxylation (lead tetraacetate, cupric acetate) gave a 3:1 mixture of esters 18 and 2 which was converted to the Queen Substance 1.
- Dhokte, U. P.,Rao, A. S.
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p. 355 - 368
(2007/10/02)
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- BIS(ARYLSULFONYL)METHANE : A VERSATILE SYNTHON IN PHEROMONE SYNTHESIS
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(E)-9-oxo-2-decenoic acid (queen substance) (1); (E)-3,7-dimethyl-2,7-octadienyl propionate (2) and (E)-3,7-dimethyl-2-octene-1,8-diol (3) are easily synthesized via sequential alkylation of bis-(arylsulfonyl)methane 4 with 1,4-allylic substrates 7 and a second electrophile such as 4,4-(ethylenedioxy)pentyl iodide and ethyl 2-methylallyl carbonate.
- Ferroud, D.,Gaudin, J. M.,Genet, J. P.
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p. 845 - 846
(2007/10/02)
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- LA REACTION DE WITTIG-HORNER EN MILIEU HETEROGENE VI. SELECTIVITE DE LA REACTION SUR DES COMPOSES BIFONCTIONNELS
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Heterogenous media of low basicity (K2CO3 or KHCO3), liquid-liquid or solid-liquid allow the Wittig-Horner reaction of fragile and unprotected aldehydes (hydroxyaldehydes, nitroaldehyde and ketoaldehydes) with excellent yields.The reaction is applied to the synthesis of Royal Jelly acid and Queen Substance of Honey bee.
- Villieras, Jean,Rambaud, Monique,Graff, Micheline
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- WITTIG-HORNER REACTION IN HETEROGENOUS MEDIA VII. A NEW STRATEGY FOR THE TOTAL SYNTHESIS OF THE ROYAL JELLY ACID AND THE QUEEN SUBSTANCE OF HONEY-BEE
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A new general scheme for the preparation of Royal Jelly acid and Queen Substance of honey-bee, including, as the key steps, copper I catalyzed addition of functional (protected alcohol and ketone) Grignard reagents to acrolein diethylacetal, and the Wittig-Horner reaction of unprotected 8-hydroxyoctanal and 7-oxo-octanal with triethylphosphonoacetate in water, in the presence of potassium carbonate.
- Villieras, J.,Rambaud, M.,Graff, M.
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p. 569 - 580
(2007/10/02)
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- Synthesis of Queen Bee and Cabbage Looper Pheromones from Aleuritic Acid
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The common intermediate in the syntheses of the two title compounds (VI and VIII) is 7-hydroxyaldehyde (II), obtained by the cleavage of α-diol of aleuritic acid (I) with NaIO4.II on Grignard reaction with MeMgI followed by pyridinium chlorochromate oxidation of the resulting diol (IV) gives the ketoaldehyde (V).The latter on malonic acid condensation affords the pheromone (VI).II on stereoselective olefination gives the olefinic alcohol (VII), which on acetylation yields the pheromone (VIII).
- Chattopadhyay, A.,Mamdapur, V. R.,Chadha, M. S.
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p. 158 - 159
(2007/10/02)
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- A NOVEL SYNTHESIS OF ROYAL JELLY ACIDS AND QUEEN SUBSTANCE BY THE FIVE CARBON HOMOLOGATION USING β-VINYL-β-PROPIOLACTONE
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10-Hydroxy-(E)-2-decenoic acid, (E)-2-decenedioic acid (Royal jelly acids), and 9-oxo-(E)-2-decenoic acid (queen substance) were synthesized via 10-hydroxy-3-decenoic acid and 9,9-ethylenedioxy-3-decenoic acid, respectively, prepared easily by the regioselective ring-opening reaction of β-vinyl-β-propiolactone with Grignard reagents in the presence of copper(I) catalyst.
- Fujisawa, Tamotsu,Sato, Toshio,Itoh, Toshiyuki
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p. 219 - 220
(2007/10/02)
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