Synthesis of racemic 10-methyltridecan-2-one,the sex pheromone ofDiabrotica undecimpunctata

A new synthesis of racemic 10-methyltridecan-2-one, the sex pheromone ofDiabrotica undecimpunctata Howardi has been effected. “InterBAV” Scientific Production Company RM, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 558–560, July–August, 1994.     

Synthesis of the racemic sex pheromone of Pseudococcus comstocki

The synthesis of the acetate of 2,6-dimethylhepta-1,5-dien-3-ol — the sex pheromone of the Comstock bug — has been carried out by condensing isobutenyllithium with 3,4-epoxy-2-methylbut-1-ene and acetylating the 2,6-dimethylhepta-1,5-dien-3-ol formed. The overall yield of pheromone was 46%.N. D. Zelinski Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow. All-Union Scientific-Research Institute of Biological Methods of Plant Protection, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 132–134, January–February, 1989.     

Stereoselective synthesis of (R)-10-methyltridecan-2-one,the sex pheromone of the southern corn rootworm,using (4S)-benzylthiazolidinethione as a chiral auxiliary

The stereoselective synthesis of (R)-10-methyltridecan-2-one, the sex pheromone of the southern corn rootworm, was carried out in 20.7% overall yield based on (4S)-benzylthiazolidinethione (five steps). In the crucial step, the stereogenic center was generated by an asymmetric Michael addition using enantiomerically pure (4S)-benzylthiazolidinethione as a chiral auxiliary.     

Asymmetric synthesis of a sex pheromone (3S,5R,6S)-3,5-dimethyl-6-isopropyl-3,4,5,6-tetrahydropyran-2-one

An Oppolzer anti-aldol approach for the synthesis of the sex pheromone (3S,5R,6S)-3,5-dimethyl-6-isopropyl-3,4,5,6-tetrahydropyran-2-one is reported.     

A study of the sex pheromone ofTortrix viridana

cis-Tetradec-ll-en-l-ol acetate has been isolated from an extract of the sex pheromone of the green oak tortrixTortrix viridana L., and has proved to be attractive under sexual conditions for the males of this species.All-Union Scientific-Research Institute of Biological Methods of Plant Protection, Kishinev, Moldles Moldavian Forestry Scientific-Production Amalgamation, Bendery, and All-Union Scientific-Research Institute of Chemical Means of Plant Protection, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 645–649, September–October, 1981.     

Synthesis of 6Z,8E-heneicosadien-11-one, a sex pheromone of the painted apple moth, Teia anartoides

6Z,8E-Heneicosadien-11-one, a sex pheromone of the painted apple moth, Teia anartoides has been prepared in seven steps from 1,2-epoxydodecane in an overall yield of 25%.     

Synthesis of racemic 5,9-dimethylheptadecane,the sex pheromone of Leucoptera scitella (Zeller) (Lepidoptera: Lyonetidae)

A new synthesis of racemic 5,9-dimethylheptadecane, from the readily available geranyl acetate, has been effected. Field trials have revealed its high attraction activity forL. scitella males.     

Synthesis of racemic 5,9-dimethylheptadecane, the sex pheromone of Leucoptera scitella (Zeller) (Lepidoptera: Lyonetidae)

A new synthesis of racemic 5,9-dimethylheptadecane, from the readily available geranyl acetate, has been effected. Field trials have revealed its high attraction activity forL. scitella males.All-Union Scientific-Research Institute of Biological Methods of Plant Protection, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 844–847, November–December, 1991.     

Synthesis ofZ-11-octadecenal,the sex pheromone of the wax moth

A new synthesis ofZ-11-octadecenal, the sex pheromone of the wax mothAchroia grisella starting from methyl 10-undecenoate is elaborated.     

A simple and cost effective synthesis of 3,11-dimethylnonacosan-2-one, a female sex pheromone of the German cockroach

A convenient synthesis of 3,11-dimethylnonacosan-2-one (1) is described. Our strategy involves the use of well known C-alkylation and ethyl acetoacetate synthesis reactions as key steps. We expect that this method will prove to be useful for large scale preparation of 1 and modification of dimethylnonacosanones.     

Synthesis of (-)-periplanone-B a sex pheromone component of the American cockroach (periplaneta americana)

The naturally occurring (-)-enantiomer of periplanone-B was synthesized stereoselectively starting from (S)-3-cyclohexene-1-carboxylic acid. The crystalline pheromone was obtained in 12% overall yield through 18 steps.     

Synthesis of dodec-10E-en-1-yl acetate — The sex pheromone of Lithocolletis blancardella

Dodec-10E-en-1-yl acetate — the sex pheromone of the apple leaf miner moth — has been obtained by a four-stage synthesis from monomethyl azelate and crotyl acetate. Its IR, PMR, and mass spectra are given.A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 537–539, July–August, 1990.     

Insect pheromones and their analogs. LVII. Synthesis of the racemic analog of the sex pheromone of pine sawflies of the generaDiprion andNeodiprion

A new route has been developed to the selective transformations of 1,1-dimethoxy-4-methyl-8-oxonon-4Z-ene —a product of the partial ozonolysis of 1,5-dimethylcycloocta-1Z, 5Z-diene—leading to (±)-3,7-dimethylpentadec-2-yl acetate, the racemic analog of the sex pheromone of pine sawflies of theDiprion andNeodiprion genera.     

Synthesis of dodec-10E-enyl acetate — the sex pheromone ofPhyllonorycter blancardella (Lepidoptera: Gracillariidae)

Dodec-10E-enyl acetate has been synthesized from undecenoic acid. Field trials have shown its high attractiveness for Phyilonorycter blancardella males.Institute of Biological Plant Protection, Academy of Sciences of Moldova, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 96–98, January–February, 1996. Original article submitted April 17, 1995.     

Synthesis of racemic domincalure — The aggregation pheromone of the lesser grain borerRhyzopertha dominica

The sec- amyl esters of 2-methylpent-2E-enoic and 2,4-dimethylpent-2E-enoic acids, constituting the aggregation pheromone of the lesser grain borerRhyzopertha dominica, have been synthesized sterospecifically in high yield from the products of the aldol condensation of propionaldehyde and isobutyraldehyde. The 2-methyl-and 2,4-dimethylpent-2E-enals were oxidized to the corresponding acids, which were converted into the chlorides and these into the corresponding sec-amyl esters. The geometric purity of the products was shown by their PMR spectra (250 MHz).N. D. Zelinskii Institute of Organic Chemistry, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 107–110, January–February, 1985.     

(3Z, 6Z)-9S, 10R-环氧-二十一碳双烯:美洲白蛾性信息素的合成

本文报道合成美洲白蛾性信息素(3Z-6Z)-9S, 10R-环氧-二十一碳双烯(1)的路线。从双乙烯甲醇出发, 经过十步合成到1, 总得率为16.85。     

Synthesis and absolute stereochemistry of serricornin [(4S,6S,7S)-4,6-dimethyl-7-hydroxy-3-nonanone] : The sex pheromone of the cigarette beetle

The absolute stereochemistry o serricornin (4,6-dimethyl-7-hydroxy-3-nonanone) was established as 4S, 6S, 7S by synthesizing both (4S, 6S, 7S)-isomer and its antipode. Only the natural enantiomer was bioactive.     

Synthesis of the sex pheromone of the grain moth Ephestia elutella

A most convenient synthesis of tetradeca-9Z,12E-dien-l-ol and its acetate — components of the sex pheromone of the grain moth — has been carried out on the basis of a scheme for obtaining a cis-1,trans-4-dienic system.     

Synthesis of racemic and optically active forms of lineatin,the unique tricyclic pheromone of trypodendron lineatum (olivier)

(±) - 33,7 - Trimethyl - 2,9 - dioxatricyclo[3.3.1.0^4,7]nonane 1 and (±) - 3,3,7 - trimethyl - 2,9-dioxatricyclo [4.2.1.0^4,7]nonane 2 were synthesized. The former was shown to be (±)-lineatin, an ambrosia beetle pheromone. A selective synthesis of (±)-lineatin was devised, which was modified to yield the both enantiomers of lineatin via optical resolution of an intermediate.