Enantiodivergent synthesis of both enantiomers of gypsy moth pheromone disparlure

Enantiodivergent synthesis of both (-)- and (+)-disparlure, a bioactive pheromone, possessing a cis-epoxide has been accomplished. The key step involves the cross metathesis of a chiral homoallylic alcohol derived from l-(+)-tartaric acid.     

双乙烯基甲醇的不对称环氧化合成午毒蛾性信息素

双乙烯基甲醇经过 Sharpless 不对称环氧化反应合成到高光学纯的午毒蛾Porthetria dispar 性信息素(7R,8S), 对映体过量大于99%, 总产率达43.9%。     

Stereoselective synthesis of the both enantiomers of disparlure,the pheromone of the gypsy moth

The both enantiomers of disparlure [(7R, 8S)-(+)-epoxy-2-methyloctadecane and its (7S,8R)-(?)-isomer] were synthesized from (2R, 3R)-(+)-tartaric acid in a stereoselective manner. (+)-Disparlure was found to be biologically active.     

桃潜蛾性信息素的合成研究

(-)-莰烷磺内酰胺手性助剂与巴豆酸酰氯作用生成N-反式丁烯酰基衍生物(4),进而与n-C~4H~9MgBr进行Michael加成反应,发现在CuBr.Me~2S存在下,产物以S构型为主,且化学产率明显提高。经六步合成了桃潜蛾性信息素(S)-14-甲基-1-十八碳烯(1)及其对映异构体(R)-1。     

Concise asymmetric synthesis of the sex pheromone of the tea tussock moth

A concise asymmetric total synthesis of the sex pheromone of the tea tussock moth has been achieved from commercially available starting materials. The chiral moiety was introduced by Evans’ template and the key CC bond construction was accomplished through Julia-Kocienski coupling and Wittig olefination. The salient characteristic of our synthetic route is that it is protecting a group free.     

Studies on the identification and synthesis of insect pheromone: XVI. Synthesis of the optically active sex pheromone of gypsy moth and its three other optical isomers

The sex pheromone of gypsy moth (+)-(7R, 8S)-7,8-epoxy-2-methyl-octadecane (la) and its three other optical isomers lb—d were synthesized stereoselectively from (+)-(R)-glyceraldehyde acetonide (2), obtained from (+)-mannitol, in 9—10 steps in an overall yield of 20—30%.     

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 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 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.A. S. Sadykov Institute of Bioorganic Chemistry, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, Vol. 6, pp. 834–840, November–December, 1989.     

Stereoselective synthesis of the Paulownia bagworm sex pheromone

According to our retrosynthesis, the main chain of the target molecule could be constructed using a C5 + C7 + C5 strategy. The key induction reaction afforded chiral methyl group moieties using different Evans templates with different configurations. Li_2 Cu Cl_4was effectively employed in the Csp~3 Csp~3 coupling protocol. The target molecular was obtained in a 12.6% overall yield with nine steps in the longest linear route.     

Insect pheromones and their analogs II. Synthesis of the sex attractant of the gypsy moth - d,l-disparlure

Summary A new route for the synthesis of 2-methyl-Z-7,8-epoxyoctadecane — the attractant ofPorthetria dispar — has been developed which uses as the starting compounds linear oligomers of butadiene and isoprene with methyl acrylate.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 792–795, November-December, 1978. Original article submitted July 25, 1978.