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 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 10,14-dimethyloctadec-1-ene, 5,9-dimethyloctadecane, and 5,9-dimethylheptadecane, the sex pheromones of female apple leafminer

The stereoselective synthesis of (10R,14R)-10,14-dimethyloctadec-1-ene (1), (5R,9R)-5,9-dimethyloctadecane (2), and (5R,9R)-5,9-dimethylheptadecane (3) the sex pheromone components of female apple leafminer was accomplished by reductive elimination tosyl and isonitrile groups of dialkylated tosylmethyl isonitrile. The key steps involved were dialkylation of TosMIC with 1-iodo 2-methyl alkanes, which were derived from Evan's alkylation of chiral auxiliary and subsequent reduction.     

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 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 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.     

Isolation and identification of the sex pheromone of females of Heliothis maritima (Lepidoptera,Noctuidae)

Four components have been isolated from an extract of the sex pheromone of the mothHeliothis maritima and have been identified: hexadecanal, hexadec-cis-11-enal, hexadec-cis-9-enal, and hexadec-cis-11-en-1-ol. All-Union Scientific-Research Institute for Biological Methods of Plant Protection, Kishinev. Don Zonal Scientific-Research Institute of Agriculture. Don Scientific-Production Combine. Ecology Division of Lund University, Lund, Sweden. Translated from Khimiya Priorodnykh Soedinenii, No. 4, pp. 574–577, July–August, 1991.     

Isolation and identification of the sex pheromone of females of Heliothis maritima (Lepidoptera, Noctuidae)

Four components have been isolated from an extract of the sex pheromone of the mothHeliothis maritima and have been identified: hexadecanal, hexadec-cis-11-enal, hexadec-cis-9-enal, and hexadec-cis-11-en-1-ol.All-Union Scientific-Research Institute for Biological Methods of Plant Protection, Kishinev. Don Zonal Scientific-Research Institute of Agriculture. Don Scientific-Production Combine. Ecology Division of Lund University, Lund, Sweden. Translated from Khimiya Priorodnykh Soedinenii, No. 4, pp. 574–577, July–August, 1991.     

Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)

The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hübner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hübner).     

Physicochemical characterization of chitin from the Mediterranean flour moth,Ephestia kuehniella Zeller (Lepidoptera: Pyralidae)

Moth chitin was extracted from adult of the Mediterranean flour moth by alkali-acid treatment and its characteristics were investigated and compared with shrimp chitin because the specific applications of chitin is directly associated with its physicochemical properties. The results revealed that the moth contained significant amounts of chitin but lower amounts of minerals. Fourier transform infrared spectroscopy (FT-IR), elemental analysis (EA), scanning electron microscopy (SEM) and energy dispersive x-ray diffraction (EDX) were used to investigate physicochemical characteristics of chitin samples. FT-IR spectra revealed that the moth chitin had α-chitin form (anti-parallel chains) with respect to the different orientations of its microfibrils. The degree of acetylation of chitin from moth and shrimp calculated using the FT-IR stretching bands were 70.82% and 71.42%, respectively. The SEM observation exhibited the presence of fibrillar material and porous structures in surface of the chitin samples. EDX analysis revealed that the main elements present in the moth chitin (beyond C, O and N) were Br (10.5%) and Si (9.7%). Our study of enzymatic activity toward colloidal chitin as substrate showed that the extracted chitin from E. kuehniella had high chemical purity as well as commercial chitin.     

Synthesis of the acetate of (±)-2,6-dimethylhepta-1,5-dien-3-ol — The racemic form of the sex pheromone of Pseudococcus comstocki

4-Methylpent-3-enal has been synthesized by the dehydration of trans-2-(1-hydroxy-1-methylethyl)-1-methoxycyclopropane, and this has been brought into reaction with propen-2-ylmagnesium bromide. Acetylation of the carbinol so formed gave the acetate of (±)-2,6-dimethylhepta-1,5-diene-3-ol — the racemic form of the sex pheromone of the Comstock mealybug.Scientific-Research Institute of Physicochemical Problems, V. I. Lenin Belorussian University, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 747–748, September–October, 1988.     

(R)-和(S)-石蚕蛾属于信息素的合成

以樟脑衍生物(-)-莰烷磺内酰胺为原料,经N-(E-2-烷烯酰基)莰烷-10,2-磺内酰胺与烷基格氏试剂的不对称Michael加成反应,LiAlH4还原断裂,3-甲基已醇的碘代反应及有机镉试剂与丙酰氯的偶联反应制得(R)-和(S)-石蚕蛾雄性性信息素6-甲基于-3-壬酮,其光学纯度达96%ee以上。     

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.     

(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 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.     

Synthesis of citrophilus mealybug sex pheromone using chrysanthemol extracted from Pyrethrum (Tanacetum cinerariifolium)

A commercial pyrethrum extract was used as a source of chrysanthemol for the synthesis of the citrophilus mealybug (Pseudococcus calceolariae) sex pheromone. The chrysanthemic acid esters (pyrethrins I) were isolated and subsequently reduced to obtain chrysanthemol, which was used for ester pheromone synthesis. Field tests showed that the pheromone synthesized using plant-derived chrysanthemol was as attractive to male P. calceolariae as the pheromone obtained using a commercial isomeric chrysanthemol mixture.     

Radical mediated stereoselective synthesis of meso-7,11-dimethylheptadecane, a female sex pheromone component of the spring hemlock looper and the pitch pine looper

meso-7,11-Dimethylheptadecane, a female sex pheromone component of the spring hemlock looper and the pitch pine looper, was synthesized from ethyl 2-(bromomethyl)propenoate in nine steps and 14% overall yield. The key step in the synthesis is the highly diastereoselective chelation-controlled radical reaction of diethyl 4-benzyloxy-2,6-dimethyleneheptanedioate with pentyl iodide performed in the presence of 6 equiv of MgBr₂·OEt₂.     

A simple synthesis of 4E,7Z-tridecadien-1-yl acetate,a component of the sex pheromone of the potato mothPhtorimaea operculella (Lepidoptera:Gelehiidae)

A simple, five-step synthesis of the title compound was developed starting from commercially available 2,4-nonadienal. The overall yield of the pheromone is 29%, and the geometric purity of the ⁴ and ⁷ double bonds is 95%. TheZ configuration of the ⁷ bond results from the 1,4-cis-hydrogenation of the intermediate 1,4,6-undecatrien-3-ol in the presence of an (arene)chromium tricarbonyl complex, while theE configuration of the ⁴ bond arises in the Claisen-Johnson rearrangement occuring in the reaction of 1,5Z-undecadien-3-ol with trimethyl orthoacetate.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2350–2353, September, 1996.     

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.     

Insect pheromones : Synthesis of chiral sex pheromone components of several species of trogoderma (coleoptera: dermestidae)

The (S)-enantiomers of (Z)- and (E)-14-methyl-8-hexadecen-1-ol, 1 and 4, respectively, and of (Z)- and (E)-14-methyl-8-hexadecenal, 6 and 7, respectively, which are sex pheromone components of dermestid beetles, have been synthesized in high optical purity starting from optically pure (S)-2-methyl-1-butanol. The preparation of 1 has been carried out using a new general method for reducing stereoselectively and in high yield ω-alkynols to the corresponding (E)-alkenols. The rotatory power of optically pure 1, 4, 6 and 7 has been established.