- Insect pheromones and their analogs. LVIII. Synthesis of hexadeca-7Z,11E-dien-1-yl acetate - A component of the sex pheromones of Pectinophora gossypiella and Sitotroga cerealella
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A new synthesis of hexadeca-7Z,11E-dien-1-yl acetate - a component of the sex pheromones of the pink bollworm (Pectinophora gossypiella) and the Angoumois grain moth (Sitotroga cerealella) - is proposed that is based on a thermal Claisen rearrangement. Scientific-Research Institute of Small-Tonnage Chemical Products and Reagents, Ufa, fax 8-(3472) 43 17 31.
- Odinokov,Vakhidov,Shakhmaev,Zorin
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p. 186 - 188
(2007/10/03)
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- STEREOSPECIFIC SYNTHESIS OF COMPONENTS OF THE NATURAL SEX PHEROMONE OF Pectinophora gossypiella
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A multistage stereospecific synthesis of components of the natural pheromone was realized.Conditions were found for stereospecific trans-reduction of the triple bonds.A procedure was developed for regiospecific dehydrohalogenation of 1,2-dibromoalkanes.Conditions giving the Z and E isomers in ratio of 96 : 4 were found for the Wittig reaction.
- Matveeva, E. D.,Kvasha, M. P.,Kurts, A.L.
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p. 1017 - 1021
(2007/10/02)
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- PHEROMONES OF INSECTS AND THEIR ANALOGS XXXIII. SYNTHESIS OF HEXADEC-7Z,11E-DIEN-1-YL ACETATE - THE SEX PHEROMONE OF Sitotroga cerealella AND A COMPONENT OF THE SEX PHEROMONE OF Pectinophora gossypiella
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From cyclohexene and caproaldehyde, using ozonolysis and the Knoevenagel reaction, we have synthesized hexadeca-7Z,11E-dien-1-yl acetate - the sex pheromone of Sitotroga cerealella and a component of the sex pheromone of Pectinophora gossypiella.
- Odinokov, V. N.,Ishmuratov, G. Yu.,Ladenkova, I. M.,Botsman, L. P.,Kargapol'tseva, T. A.,Tolstikov, G. A.
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p. 621 - 623
(2007/10/02)
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- SYNTHETIC INVESTIGATIONS IN THE FIELD OF INSECT ATTRACTANTS (SEX ATTRACTANTS). X. SYNTHESIS OF THE ACETATES OF CIS-7,CIS-11- AND CIS-7,TRANS-11-HEXADECADIEN-1-OL, THE SEX PHEROMONES OF THE PINK BOLLWORM MOTH Pectinophora gossypiella S. (LEPIDOPTERA, GELECHIIDAE) AND THE GRAIN MOTH Sit...
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The synthesis of the acetates of cis-7,cis-11- and cis-7,trans-11-hexadecadien-1-ol, which are the sex pheromones of the pink bollworm moth Pectinophora gossypiella and the Angoumois grain moth Sitotroga cerealella, and their geometric isomers on the basis of the Wittig reaction and of the unsaturated functionally ω-substituted aldehydes is described.The alkylation of the dilithium derivative of 4-pentyn-1-ol by 2-(6-bromohexyloxy)tetrahydropyran in a mixture of liquid ammonia and THF gave a 40percent yield of 11-(2-tetrahydropyranyloxy)-4-undecyn-1-ol, which was hydrogenated selectively to 11-(2-tetrahydropyranyloxy)-cis-4-undecen-1-ol or was reduced to 11-(2-tetrahydropyranyloxy)-trans-4-undecen-1-ol.Both alcohols were oxidized by pyridinium chlorochromate to 11-(2-tetrahydropyranyloxy)-cis-4-undecenal and 11-(2-tetrahydropyranyloxy)-trans-4-undecenal.The reaction of both aldehydes with amyltriphenylphosphonium bromide under stereocontrolled conditions followed by acetolysis gave the acetates of cis-7,cis-11-, cis-7,trans-11-, trans-7,cis-11-, and trans-7,trans-11-hexadecadien-1-ols and a mixture of the acetates of cis-7,cis-11- and cis-7,trans-11-hexadecadien-1-ol (gossyplure).
- Kovalev, B. G.,Avdeeva, L. A.,Sorochinskaya, A. M.
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p. 641 - 646
(2007/10/02)
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- A Practical Synthesis of Sex Pheromones of Pink Bollworm: Gossyplure
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The practical synthesis of (Z,Z) and (Z,E)-7,11-hexadecadienyl acetates, sex pheromones of pink bollworm (gossyplure) is described.
- Yadav, J. S.,Upender, V.,Shekharam, T.,Reddy, E. Rajarathnam
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p. 1012 - 1014
(2007/10/02)
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- STEREOSELECTIVE AND VERSATILE APPROACH FOR THE SYNTHESIS OF GOSSYPLURE AND ITS COMPONENTS
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Efficient synthetic routes to gossyplure and its components (1a and 1b) were formulated.The three key units viz the alkynol 3, the bromide 5, and the alkanal 13 were derived from easily accessible starting materials.Alkylation of 3 with 5, and subsequent semihydrogenation followed by oxidation, provided the C11-alkenal 8 which was subjected to a stereocontrolled Wittig reaction with a C5-phosphonium salt, to yield directly the disired pheromone (1a + 1b).The synthesis of its individual components involved the manipulation via an acetylenic intermediate, viz the alkynol 14 which was obtained through alkylation of 3.A sequence of well-established reactions on 14, then provided the corresponding (E)- and (Z)-alkenylphosphonium salts which upon a (Z)-specific Wittig olefination with the C7-aldehyde (13), led to the stereoselective synthesis of 1a and 1b.
- Joshi, N. N.,Mamdapur, V. R.,Chadha, M. S.
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p. 3285 - 3290
(2007/10/02)
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- THE STEREOSELECTIVE α-ALKYLATION OF CHIRAL β-HYDROXY ESTERS AND SOME APPLICATIONS THEREOF
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The stereoselectivity of the α-alkylation of chiral β-hydroxy ester is discussed.The configuration of the alkylated product was proved chemically (Scheme 2) .A one pot aldol-alkylation reaction was developed leading stereoselectively to racemic(S*,S*)-α-alkyl-β-hydroxy ester (Scheme 3,4) .Baker's yeast reduction of 2-alkyl-3-keto ester led to valuable chiral (2RS,3S)-intermediates, which were converted via the corresponding dianion to compounds with a chiral quaternary C atom (Scheme 6) .Synthetic applications of the above findings are shown in the synthesis of various chiral compounds (Scheme 8 and 9) .
- Frater, G.,Mueller, U.,Guenther, W.
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p. 1269 - 1278
(2007/10/02)
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- 4,8-Tridecadien-1-ol,4 cis,8 cis,trans
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Synthesis of the sex pheromone, (7Z,11Z/E)-7,11-hexadecadienyl acetate, of the pink bollworm moth, Pectinophora gossypiella, and intermediates therefor.
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