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1.
A simple synthesis of a diastereomeric mixture of 7-hydroxy-4,6-dimethylnonan-3-ones was carried out. In the biological action,
it is an analog of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne).
Dedicated to Academician N. K. Kochetkov on the occasion of his 90th birthday.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1218–1221, May, 2005. 相似文献
2.
Highly enantiomerically pure (4S, 5E)-4-bromomethylhept-5-enenitrile was prepared from (S)-ethyl lactate by a six-step procedure involving a rearrangement of chiral cyclopropylcarbinol. This product was used for
the synthesis of the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi), (10R)-10-methyltridecan-2-one.
For preliminary communication, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 151–155, January, 2000. 相似文献
3.
(R)-4-Menthenone in the synthesis of optically pure sex pheromone of the peach leafminer moth (Lyonetia clerkella) 总被引:1,自引:0,他引:1
Kharisov R. Ya. Latypova E. R. Talipov R. F. Muslukhov R. R. Ishmuratov G. Yu. Tolstikov G. A. 《Russian Chemical Bulletin》2003,52(10):2267-2269
The synthesis of (14S)-methyloctadec-1-ene, sex pheromone of the peach leafminer moth (Lyonetia clerkella), is described to demonstrate a new potential of the synthetic use of (R)-4-menthenone. 相似文献
4.
Highly enantiomerically pure (4S, 5E)-4-bromomethylhept-5-enenitrile was prepared from (S)-ethyl lactate by a six-step procedure involving a rearrangement of chiral cyclopropylcarbinol. This product was used for
the synthesis of the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi), (10R)-10-methyltridecan-2-one.
For preliminary communication, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 151–155, January, 2000. 相似文献
5.
Total synthesis of 3-methylhept-2(Z)-enoic acid, a sex pheromone of the dry bean beetleCallosobruchus analis, has been performed using a previously developed highly stereoselective method of the construction of disubstituted (Z)-methylolefins based on the higher thermodynamic stability of (E)-isomers of α,β-disubstituted acroleins.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1385–1388, July, 1999. 相似文献
6.
G. Yu. Ishmuratov R. Ya. Kharisov M. P. Yakovleva R. R. Muslukhov E. G. Galkin V. S. Shmakov T. V. Khakimova G. A. Tolstikov 《Russian Chemical Bulletin》2000,49(4):717-721
An enantioselective (ee−50%) four-step synthesis of (S)-6-methylhept-5-en-2-ol (“sulcatol”), which is the aggregation pheromone ofGnathotrichus sulcatus, from 3S,7-dimethylocta-1,6-diene was developed.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 713–717, April, 2000. 相似文献
7.
A formal total synthesis of 3-methylhept-2(Z)-enoic acid, a sex pheromone of the dry bean beetleCallosobruchus analis, was performed on the basis of a highly stereoselective version of the Peterson olefination of ketones developed previously
by the authors.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1389–1392, July, 1999. 相似文献
8.
G. Yu. Ishmuratov M. P. Yakovleva R. Ya. Kharisov I. M. Muslimova R. R. Muslukhov R. L. Safiullin G. A. Tolstikov 《Russian Chemical Bulletin》1997,46(5):1033-1035
An enantiospecific synthesis of (S)-(+)-3-methylheneicosan-2-one, an analog of the sex pheromone of the German cockroach (Blatella germanica L.), was carried out through selective transformations of (3R,6S)-3,7-dimethyloctane-6-olide obtained from (−)-menthonevia the Baeyer—Villiger reaction.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1071–1073, May, 1997. 相似文献
9.
G. Yu. Ishmuratov M. P. Yakovleva G. V. Zaripova L. P. Botsman R. R. Muslukhov G. A. Tolstikov 《Chemistry of Natural Compounds》2004,40(6):548-551
A novel synthesis of the promising optically pure chiral (4R)-4-methylpentanolide that is based on several regiospecific oxidative transformations of (4R)-2,4-dimethyl-1-(1-methylethyl)-1-cyclohexene, the product of addition of (–)-menthone and methylmagnesium iodide followed by acid dehydration, was proposed.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 451–453, November–December, 2004.This revised version was published online in April 2005 with a corrected cover date. 相似文献
10.
Z. G. Chrelashvili M. V. Mavrov B. I. Ugrak A. A. Kutin E. P. Serebryakov 《Russian Chemical Bulletin》1993,42(9):1593-1597
Two analogous routes to the title pheromones were elaborated based on organocuprate cross-coupling ofZ,Z-dienic electrophiles, (2Z,4Z)-1-acetoxy-2,4-heptadiene (6) and (3Z,5Z)-1-bromoctadiene (8), with -tert-butoxy-1-chloropentane and -butane, respectively. Optimal conditions for the reduction of 2,4-heptadiyn-1-ol and 3,5-octadiyn-1-ol to the respectiveZ,Z-alkadienols as precursors for the electrophiles were found. Treatment of diynols with activated zinc in aqueous alcohol provided high geometrical purity of the product (94 %). In both cases, copper-catalyzed cross-coupling afforded 1-tert-butoxy-7,9-dodecadiene (four stereoisomers), acetolysis of which gave the target pheromone contaminated by stereoisomers. In the case of allylic electrophile6, the reaction occurred with the loss of the initial configurational purity, whereas the use of homoallylic bromide8 ensured almost complete retention of the configuration of the double bonds and obtaining the target pheromone of 87 % configurational purity.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1656–1660, September, 1993. 相似文献
11.
V. N. Odinokov G. Yu. Ishmuratov M. P. Yakovleva R. L. Safiullin V. D. Komissarov G. A. Tolstikov 《Russian Chemical Bulletin》1993,42(7):1244-1245
A number of novel methyl-branched chirones were prepared starting from (–)-menthone and making use of a novel, efficient, and selective oxidant, decanepersulfonic acid (DPSA). Optically pure (4R)-methyl-1-nonanol, the sex pheromone of the larger flour beetle (Tenebrio molitor L.), was synthesized.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1301–1303, July, 1993. 相似文献
12.
G. Yu. Ishmuratov R. Ya. Kharisov O. V. Botsman V. V. Zorin G. A. Tolstikov 《Russian Chemical Bulletin》2000,49(11):1899-1901
Effective routes for the synthesis of (S)-2-acetoxytridecane, the sex pheromone of the fruit flyDrosophila mulleri, and (S)-1-methylbutyl 2-methyl- and 2,4-dimethylpent-2E-enoates, components of the aggregation pheromone of the lesser grain borerRhyzopertha dominica, were developed on the basis of (S)-4-methylhex-5-en-1-yl tosylate accessible from (S)-(+)-dihydromyreene.
Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1929–1931, November, 2000. 相似文献
13.
M. Madesclaire P. Coudert V. Gaumet V. P. Zaitsev Yu. V. Zaitseva 《Chemistry of Heterocyclic Compounds》2006,42(5):665-670
We have synthesized a series of (1R,2R,4S,5S,8S)-2,8-diaryl-4-(4-nitrophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octanes as a result
of reaction of (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediol with aromatic aldehydes. The structure of the compounds obtained
was established on the basis of 1H NMR data.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 757–763, May, 2006. 相似文献
14.
Z. G. Chrelashvili M. V. Mavrov A. V. Dolidze A. P. Voronkov E. P. Serebryakov 《Russian Chemical Bulletin》1993,42(4):734-736
Two syntheses of 7E,9Z-dodecadienyl acetate from 1,3-butadiyne were carried out using either 2E,4Z-heptadienyl acetate or 1-bromo-3E,5Z-octadiene as the key intermediates. The latter underwent organocopper cross-coupling with the respective complementary Grignard reagents (prepared from the corresponding 1-tert-butoxy--chlorohydrins) as alkylating agents.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 766–768, April, 1993. 相似文献
15.
11-Tetradecen-1-ol acetate is a mixture of geometric isomers with the Z/E-conformations in a 94:6 ratio that is used as an attractant to trap corn pests. It has a powerful attractive action similar
to that of an isomeric mixture of 11-tetradecenyl acetate with the Z/E-conformation in a 95:5 ratio that was extracted from the peritoneal cavity of male Ostrinia nubilalis Hubner in Xinjing (PRC).
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Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 177–178, March–April, 2008. 相似文献
16.
G. Yu. Ishmuratov M. P. Yakovleva V. A. Ganieva R. Ya. Kharisov R. R. Gazetdinov A. M. Abulkaramova G. A. Tolstikov 《Chemistry of Natural Compounds》2006,42(1):92-95
Three new approaches to the synthesis of 1-bromo-3S-methylundecane, a key synthon in the synthesis of (S,S,S)-diprionylacetate, a sex pheromone of pine sawflies of the genera Diprion and Neodiprion, were proposed based on chemo-and stereoselective transformations of L-(-)-menthol derivatives.
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Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 73–76, January–February, 2006. 相似文献
17.
M. Madesclaire V. P. Zaitsev J. V. Zaitseva S. Kh. Sharipova 《Chemistry of Heterocyclic Compounds》2007,43(10):1325-1332
A synthesis is reported for (4R,5R)-and (4S,5S)-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-ones and (1′R,4R)-and (1′S,4S)-4-[hydroxy(4-nitrophenyl)methyl]oxazolidin-2-ones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols. The effect of the experimental conditions on the formation of these compounds
was studied.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1562–1570, October, 2007. 相似文献
18.
V. I. Bykov A. R. Goletiani T. A. Butenko E. Sh. Finkelshtein 《Russian Chemical Bulletin》2004,53(11):2650-2652
A new synthesis of (Z,E)-undec-5-enoic acids with the natural isomer composition Z/E = 85 : 15, the sex pheromone of the varied carpet beetle Anthrenus verbasci was developed based on co-metathesis of cycloocta-1,5-diene and ethylene.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2540–2542, November, 2004. 相似文献
19.
Stereospecific synthesis of the sex pheromone of the passionvine mealybug, Planococcus minor 总被引:1,自引:0,他引:1
Jocelyn G. Millar 《Tetrahedron letters》2008,49(2):315-317
A short and completely stereospecific synthesis of (E)-2-isopropyl-5-methyl-2,4-hexadienyl acetate, the very recently identified sex pheromone of the passionvine mealybug Planococcus minor, is described. In the key step, CuI-catalyzed anti-addition of a Grignard reagent to a propargyllic alcohol intermediate gave the required trisubstituted alkene with 100% regio- and stereospecificity. The stereochemical purity of the pheromone is critically important because the (Z)-isomer is a powerful behavioral antagonist. 相似文献
20.
J. Couquelet M. Madesclaire F. Leal V. P. Zaitsev S. Kh. Sharipova 《Chemistry of Heterocyclic Compounds》2001,37(7):898-902
The reaction of (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediol with glutaraldehyde has been studied. It has been established on the basis of AM1 and PM3 calculations and 1H NMR spectra recorded in the presence of the shift reagent Eu(fod)3 that (1S,3S,4S,7R,11R)-3-(4-nitrophenyl)-11-aza-2,6-dioxatricyclo[5,3,1,04,11]undecane is formed as the result of the reaction. 相似文献