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%。     

昆虫信息素结构鉴定与合成 XXI, 淡色库蚊产卵引诱信息素四个光学异构体的立体选择性合成

应用Sharless不对称环氧化反应,合成淡色库蚊产卵引诱信息素的所有四个光学异构体1a～1d, e.e.96～97%. 从炔醇2出发到1a～1d的总得率为15～20%.     

Studies on the identification and syntheses of insect pheromones XXI stereoselective synthesis of all the possible optical isomers of the mosquito oviposition attractant pheromone

All the four optical isomers of the oviposition attractant pheromone of the mosquito $\text{Gulex pipiens fatigans}$ were synthesized via Sharpless asymmetric epoxidation.     

Enzymatic resolution of 2,3-epoxyalcohols,intermediates in the synthesis of the gypsy moth sex pheromone

An efficient resolution of 2,3-epoxyalcohols 2a-b were obtained both by enzymatic hydrolysis and transesterification in organic solvent: (25,3R) 2b and (2R,35) 2a thus obtained are chiral synthons for the synthesis of (+)- Disparlure 1.     

昆虫信息素结构鉴定和合成的研究XXV.用三乙胺作烯铜锂试剂配位体合成棉铃虫和午毒蛾性信息素

Tri-Et amine liganded vinyl cuprate was employed in the synthesis of the major components of the sex pheromone of old world bollworm moth (Heliothis armigera), cis-7-hexadecenal (I) and cis-11-hexadecenal (II), and gypsy moth (Porthetria dispar), 7,8-epoxy-2-methyloctadecane (III), with high Z purity (99.9%). The overall yields of I and II from octyllithium and BuLi were 70% in 3 steps, and that of III from decyllithium was 60% in 2 steps.     

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。     

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.     

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.     

Studies on the identification and synthesis of insect pheromone: XXIV. Synthesis of (7R, 8S)-(+)- and (7S, 8R)-(−)-sex pheromone of gypsy moth and stereochemistry of β-hydroxysilane

Condensation of the epoxy aldehyde 2 or 2 prepared by Sharpless asymmetric epoxydation in 96—97% yield, with trimethylsilane lithiated 3 gave 7 or 7 ′, which after transformation to the corresponding acetoxyl compound 8 or 8 ′ afforded the title compound 1a or 1b via β-acetoxysilane elimination and catalytic homogeneous hydrogenation. The configurations of the stereoisomers 7 and 7 ′ were determined.     

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.     

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.     

昆虫信息素研究 I: 谷斑皮蠹性信息素14-甲基-顺-8-十六碳烯醛的立体选择合成

研究了谷斑皮蠹性信息素的主要活性组份为14-甲基-8-十六碳烯醛, 报导了新合成路线, 其关键步骤是以2-溴丁烷的格氏试剂与1,4-二溴丁烷在Li2CuCl4存在下发生偶联反应, 制得的1-溴-5-甲基庚烷, 它与金属锂、CuI和CH≡CH反应而得高纯度顺式双键构型产物, 脱保护基再经PCC氢化即得目的物14-甲基-顺-8-十六碳烯醛.     

昆虫信息素的结构鉴定与合成XX.应用不对称环氧化中的动力学拆分从消旋体合成光学活性的午毒蛾性信息素

(±-烯丙醇(2),经过不对称环氧化反应中的动力学拆分得到手性环氧醇3,e.e.92%.3经过5步反应得(7R,8S)-午毒娥性信息素(1a),总得率从3算起为60%。