- Green and Catalytic Synthesis of Dominicalure I, Major Component of the Aggregation Pheromone of Rhyzopertha dominica (Fabricius) (Coleoptera: Bostrichidae)
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(Chemical Equation Presented). A new concise and efficient catalytic synthesis of dominicalure I, the male-produced aggregation pheromone of the grain borer Rhyzopertha dominica, is herein reported. The synthetic route was designed starting from easily available propanal through an organocatalytic key step and completed with biocatalytic procedures.
- Dibello, Estefanía,Seoane, Gustavo,Gamenara, Daniela
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supporting information
p. 975 - 981
(2015/03/30)
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- A facile Zn-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from Baylis-Hillman adducts in water and its application
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A simple and efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been accomplished by treatment of the acetyl derivatives of the Baylis-Hillman adducts with Zn in saturated aq. NH 4C1 solution under reflux. The method has been utilized for the preparation of the two chiral insect pheromones, dominicalure-I and dominicalure-II, of the lesser grain borer Rhyzopertha dominica (F). Copyright
- Das, Biswanath,Chowdhury, Nikhil,Banerjee, Joydeep,Majhi, Anjoy,Mahender, Gurram
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p. 358 - 359
(2007/10/03)
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- Synthetic applications of the Baylis-Hillman reaction: Simple and convenient synthesis of five important insect pheromones
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A simple and convenient synthesis of five important insect pheromones by means of Baylis-Hillman adducts is described, i.e., of (2E,4S)-2,4-dimethylhex- 2-enoic acid (1), a mandibular-gland secretion of the male carpenter ant in the genus Camponotus, of (+)-(S)-manicone (2) and (+)-(S)-normanicone (3), two mandibular-gland constituents of Manica ants, and of (+)-dominicalure-I (6) and (+)-dominicalure-II (7), two aggregation pheromones of the lesser grain borer Rhyzopertha dominion (F). For the first time, the potential of the Baylis-Hillman chemistry for the stereoselective synthesis of trisubstituted olefins was successfully applied to the synthesis of these pheromone compounds.
- Das, Biswanath,Banerjee, Joydeep,Chowdhury, Nikhil,Majhi, Anjoy,Mahender, Gurram
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p. 876 - 883
(2007/10/03)
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- Synthesis of derivatives of (S)-2-alkanols, components of pheromones of Drosophila mulleri and Rhyzopertha dominica, from (S)-(+)-3,7-dimethylocta-1,6-diene
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Effective routes for the synthesis of (S)-2-acetoxytridecane, the sex pheromone of the fruit fly Drosophila mulleri, and (S)-1-methylbutyl 2-methyl- and 2,4-dimethylpent-2E-enoates, components of the aggregation pheromone of the lesser grain borer Rhyzopertha dominica, were developed on the basis of (S)-4-methylhex-5-en-1-yl tosylate accessible from (S)-(+)-dihydromyrcene.
- Ishmuratov,Kharisov,Botsman,Zorin,Tolstikov
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p. 1899 - 1901
(2007/10/03)
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- Synthetic application of alkyl (E)-2-tributylstannyl-2-alkenoates: Selective synthesis of (S)-1-methylbutyl (E)-2-methyl-2-pentenoate, an aggregation pheromone component of Rhyzopertha dominica and Prostephanus truncatus
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Stereoisomerically pure (S)-1-methylbutyl (E)-2-methyl-2-pentenoate (dominicalure-1), (S)(E)-11, an aggregation pheromone component for the lesser and the greater grain borers, has been efficiently synthesized from the main product of the palladium-catalyzed reaction between ethyl 2-pentynoate, 1a, and Bu3SnH, i.e. ethyl (E)-2-tributylstannyl-2-pentenoate, (E)-2a.
- Rossi,Carpita,Cossi
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p. 143 - 152
(2007/10/02)
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- Enzyme Reactions in Apolar Solvent. 5. The Effect of Adjacent Unsaturation on the PPL-Catalyzed Kinetic Resolution of Secondary Alcohols
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The effect of adjacent unsaturation on the enzyme-catalyzed kinetic resolution of secondary alcohols is studied for a series of allylic, homoallylic, propargylic, homopropargylic, and phenyl-substituted 2-alkanols, using porcine pancreatic lipase (PPL) in anhydrous Et2O.Excellent enantioselectivity (high E value) was observed for α-phenethyl alcohol (3), propargylic alcohols (8 and 11), and (E)-allylic alcohols (9 and 12), but (Z)-allylic alcohols (10 and 13) showed poor selectivity.Enantioselectivity was also low for both (E)- and (Z)-homoallylic alcohols (15 and 16), homopropargylic alcohol (14), 1-phenyl-2-propanol (6), and 4-phenyl- 2-butanol (7).The enhanced enantioselectivity observed for (E)-allylic alcohols was exploited in the synthesis of the enantiomers of both components of the aggregation pheromone of the lesser grain borer, Rhyzopertha dominica (F.).The magnitude of the enantiomeric ratio (E value) can be dramatically affected by the accuracy of the values of ees and eep used in the calculation, especially when E is large.Variation in the value of E with the optical purity of the chiral derivatizing agent used to determine ees and eep is illustrated.
- Morgan, Brian,Oehlschlager, Allan C.,Stokes, Thomas M.
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p. 3231 - 3236
(2007/10/02)
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- EFFECTIVE SYNTHESIS OF ENANTIOMERIC 2-PENTANOLS AND CHIRAL DOMINICALURES BASED ON THEM
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The (S) and (R) enantiomers of sec-amyl-2-methyl-(2E)-pentenoate and 2,4-dimethyl-(2E)-pentenoate (dominicalure 1 and dominicalure 2 respectively), which are contained in the aggregation pheromone of the lesser grain borer Rhizopertha dominica, were synthesized by the acylation of (S)- and (R)-2-pentanols. (2S)-Pentanol was obtained in five stages with an overall yield of > 50percent from (S)-ethyl lactate with cross-coupling of the p-toluenesulfonate of (2S)-(2-tetrahydropyranyloxy)-1-propanol with lithium diethylcuprate at the key stage.Zinc chloride can be used as an effective catalyst for the removal of the tetrahydropyranyl protection under mild conditions. (2R)-Pentanol was prepared by inversion of the configuration of its (S) enantiomer by the Mitsunobu method.
- Cheskis, B. A.,Shpiro, N. A.,Moiseenkov, A. M.
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p. 1613 - 1616
(2007/10/02)
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