Full-Text Search:
Home|Journal Papers|About CNKI|User Service|FAQ|Contact Us|中文
《Acta Chimica Sinica》 1984-08
Add to Favorite Get Latest Update

STUDIES ON THE IDENTIFICATION AND SYNTHESES OF INSECT PHEROMONE XVI. SYNTHESES OF THE OPTICAL ACTIVE SEX PHEROMONE OF GYPSY MOTH AND ITS THREE OPTICAL ISOMERS

LIN GUO-QIANG~* WU BI-CHI LIU LIN-YU WANG XIAN-QING ZHOU WEI-SHAN(Shanghai Institute of Organic Chemistry Academia Sinica)  
The title compounds 1a~d were synthesized from(+)-(R)-glyceraldehyde acetonide (2) obtained from mannitol in 9~10 steps in an overall yield of 20~30%. Thus, Grignard reaction of 2 with n-C_(10)H_(21)MgBr yielded a mixture of two diastereoisomers which afforded 3(erythro form, R, S) and 4 (threo form, R, R) by SiO_2 gel chromatography. The free alcohol 3 was reacted with benzyl chloride followed by acidic hydrolysis to give diol 6 which on selective tosylation followed by treatment with 0.25 M methanolic KOH gave an epoxide 8. 8 was treated with(i-hex)_2 OuLi in ether to give 9 which on removal of the benzyl protecting group followed by reaction with HBr-HOAc gave a mixture of 11a and 11b. Finally, treatment of the mixture of 11a and 11b with 0.5M methanolic KOH gave (+)-disparlure(1a). 1c and 1d were obtained from 9 by the reaction sequences as shown in the Chinese Text. The (-)-disparlure (1b) was obtained from 4 by the reaction sequences of 5'→6'→7'→8'→9'→1b.
Download(CAJ format) Download(PDF format)
CAJViewer7.0 supports all the CNKI file formats; AdobeReader only supports the PDF format.
【References】
Chinese Journal Full-text Database 2 Hits
1 Miao Jian-cai(Northeast Forestry University) Wang Zen-hua(Station of the prevention and Quarantine of Forest Diseases and Pests of Mishan Country of Heilongjiang Province) Gao Wen-tao (Forest Experimental Farm of J lin Forestry University);STUDY ON APPLIED TECHNIQUE OF SEX PHEROMONE OF GYPSY MOTH[J];Journal of Northeast Forestry University;1988-01
2 ZHANG, Chao-Xin DA, Shi-Jun ZHANG, Hua-Bing SUN, Bin LI, Ying* (State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000);Asymmetric Total Synthesis of (+)-Disparlure: (+)-(7R,8S)-cis-7,8- epoxy-2-methyloctadecane[J];Acta Chimica Sinica;2007-21
【Co-references】
Chinese Journal Full-text Database 10 Hits
1 Heng Xuemin (The Nursery of Hefei,Hefei,Anhui 230001);Investigation of Aphid Species of Garden Plant in Hefei[J];Journal of Anhui Agricultural Sciences;2004-04
2 Li Zhenyu;Yao Defu;Chen Yongmei;Feng Jihua;Yan Guozeng;Shi Juan. College of Biology,Beijing For. Univ.,100083,P.R.China.;Parasitioids and alternate hosts of Gypsy moth in Beijing area.[J];Journal of Beijing Forestry University;2001-05
3 Zhou Yousheng Shen Farong(Kuming Institute of Zoology,Academia Sinica,Kuming,650223,P.R.China)Zhao Huanping(Extension Centre for Agriculture and Animal Husbandry Techniques,Jinggu,666400,P.R.China,);Applying B.bassiana(Bala) Vuill to Control R.bowringii White[J];JOURNAL OF BEIJING FORESTRY UNIVERSITY;1998-04
4 Pu Guanqin; Du Heming; Mao Jianping(College of Biotechnology, Suzhou University,Suzhou 215151, China);STUDIES ON THE SEX PHEROMONE COMPONENTS OF MULBERRY LOOPER (Hemerophila atrilineata BUTLER)[J];ACTA SERICOLOGICA SINICA;1997-02
5 QI Hui-xia (Depr.of Agronomy,HVTTC,Changli,066600,China);Investigation of the moth pests in Qinhuangdao area,Hebei Province[J];Journal of Northeast Agricultural University;2003-04
6 Miao Jian-cai (North-Eastern Institute of Forestry) Wang Huan-lou (Jianshe Forestry Centre in Fuxin County of Liaoning Province) Zheng Zhi-tian (Forest Protection Station in Gannan County of Heilungjiang Province);STUDY ON THE ATTRACTION EFFECT AND THE BIOLOGICAL ACTIVATION OF DISPARLURE OF PORTHETRIA DISPAR L.[J];;1982-02
7 Sun Hongzhi. Zhang Guocai. Lin Tong (Northeast Forestry University. Harbin 150040); Yu Bin(Harbin University)//Journal of Northeast Forestry University.;Population Dynamics Prediction Techniques of Lymantria dispar L.[J];Journal of Northeast Forestry University;2001-01
8 Shao Ruilian, Dong Xiyang, Zhang Chunzao and Li Jifeng (Institute of Elemento-Organic Chemistry, Nankai University, Tianjin);Study of Geometric Isomers of Some Vinylphosphate Insecticides (Ⅲ)--Isomerization of (Z)-to (E)-Isomer of O,O-Diethyl-O-(1-Ethoxycarbonyl-1-Propen-2-yl) Thiophosphate[J];Chemical Research In Chinese Universities;1985-04
9 Li Zhengming.Dong Lixia,Li Guowei,Zhang Zuxin, Cao Qiuwen and Wang Suha (Institute of Elemento-Organic Chemistry,Nankai University,Tianjin)Dou Shiqi (Institute of Biophysics, Academic Sinica,Beijng);Studies on Steromers of Triadimenol (Ⅱ)[J];Chemical Research In Chinese Universities;1987-03
10 Liu Tianlin. Li Zhengming, Wang Likun, Liang Ge (The Research Institute of Elemento-Organio Chemistry, Sankai University, Tianjin);Studies on the Insect Sex Pheromones(Ⅴ)——The Synthesis of the Housefly Sex Attractant Z-9-Tricosene[J];Chemical Research In Chinese Universities;1988-05
【Secondary References】
Chinese Journal Full-text Database 10 Hits
1 MA Guo-lan et al(Biological Safety S&T College,Hunan Agricultural University,Shaoyang,Hunan 410128);Prevention and Controlling Method of Aphid and its Apptication Prospect[J];Journal of Anhui Agricultural Sciences;2006-14
2 Hao Dejun(Nanjing Agricultural University, Nanjing 210095, P. R. China); Wang Yan(Forest Pest Management and Quarantine Station of Shanghai); Dai Huaguo(Nanjing Agricultural University); Ma Fenglin, Shen Fengqin(Forest Pest Management and Quarantine Station of Shanghai);Strategy for Ecological Management of Pests in Plantations and Prospect for Control Techniques[J];Journal of Northeast Forestry University;2004-06
3 ZHU Xiaoli,GU Xiangling,ZHANG Zhiguo,KONG Xiang Zheng(College of Chemistry and Chemical Engineering,University of Jinan,Jinan 250022);PREPARATION OF INSECT SEX PHEROMONE DODECANOL CONTAINING MICROCAPSULES BY SIMPLE AND COMPLEX COACERVATIONS AND THEIR RELEASE BEHAVIOR[J];Acta Polymerica Sinica;2007-05
4 YAO Jian et al (College of Agriculture,Guangxi University,Nanning,Guangxi 530005);Study on the Eclosion and Mating Behaviors of Conopomorpha sinensis Bradley[J];Journal of Anhui Agricultural Sciences;2009-25
5 LI Hong-jun,HE Xiong-kui,ZENG Ai-jun,JIANG Shu-ren,CAO Shan(College of Science,China Agricultural University,Beijing 100094,China);Research Advance on Sex Pheromone of Gall Midge(Diptera: Cecidomyiidae)[J];Acta Agriculturae Boreali-Sinica;2008-S1
6 XIANG Yu-yong,YANG Mao-fa(Institute of Entomology,Guizhou University,Guiyang 550025,China);Progress on Study and Application of Insects Sex Pheromone[J];Hubei Agricultural Sciences;2006-02
7 ZHU, Xiao-Li GU, Xiang-Ling LIAN, Jie ZHANG, Zhi-Guo KONG, Xiang-Zheng* (College of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022);Preparation of Insect Sex Pheromone Simulacrum Dodecanol Containing Microcapsules and Its Controlled Release[J];Acta Chimica Sinica;2008-01
8 Yao Yingjuan Xue Dong Yang Changju(Institute of Urban Pest Control, Huazhong Agriculture University,Wuhan 430070, China);Advances on the Relationship between Insect Behavior and Infrochemicals[J];Journal of Huazhong Agricultural;2004-04
9 GAO Chang-qi, SUN Shou-hui, SONG Fu-qiang, CHEN Hua-feng, YAO Lu-xian, ZHANG Xiao-jun, NIU Yan-zhang, YU Yan-ping (1. Jilin Provincial Academy of Forestry Science, Changchun 130031, China; 2. Foreign Expert Bureau of Jilin Province, Changchun 130000, C;Insect sex pheromone and its application in the pest control[J];Forestry Scicnce and Technology;2001-01
10 SONG Li-wen1,ZHANG Da-ming1,LI Xing-peng1, ZHANG Kai-peng2,ZHUO Tong-tong1,ZHANG Xiao-jun1,GAO Chang-qi1(1.Jilin Provincial Academy of Forestry Sciences,Changchun,Jilin Province,130033,China;2.Jingyuetan Experimental Forest Farm of Changchun City,Changchun 130117 China);Function of bark beetle semiochemicals[J];Jilin Forestry Science and Technology;2009-01
China Proceedings of conference Full-text Database 1 Hits
1 XIA Ru-bing, WANG Si-ming, YANG Zong-wu (Institution of Chinese Agricultural Civilization, Nanjing Agricultural University, Nanjing, 210095);The Influences of Relevant Science and Technology Factors on The Development of Entomology in China[A];[C];2003
©2006 Tsinghua Tongfang Knowledge Network Technology Co., Ltd.(Beijing)(TTKN) All rights reserved