Asymmetric Synthesis of the Contact Sex Pheromone of the Emerald Ash Borer, Agrilus planipennis Fairmaire

被引：0
作者：
Yu, Shihang [1 ]
Wu, Jianwei [1 ]
Bian, Qinghua [1 ]
Wang, Min [1 ]
Zhong, Jiangchun [1 ]
机构：
[1] China Agr Univ, Dept Appl Chem, 2 West Yuanmingyuan Rd, Beijing 100193, Peoples R China
来源：
CHEMISTRYSELECT | 2023年 / 8卷 / 29期
关键词：
Agrilus planipennis Fairmaire; asymmetric synthesis; chiral propylene oxide; contact pheromone; COLEOPTERA BUPRESTIDAE; BIOLOGICAL-CONTROL;
D O I：
10.1002/slct.202302084
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Agrilus planipennis Fairmaire is a wood-boring pest of ash trees. The contact sex pheromone of this pest was synthesized from chiral propylene oxide. This asymmetric synthesis was efficient and mainly involved the ring-opening reaction of chiral propylene oxide, the stereospecific inversion of secondary tosylate and Wittig coupling of chiral aldehyde.
引用
收藏
页数：3
相关论文
共 27 条
  • [1] Rapid Spread of an Introduced Parasitoid for Biological Control of Emerald Ash Borer (Coleoptera: Buprestidae) in Maryland
    Aker, Stokes A.
    de Andrade, Rafael B.
    Duan, Jian J.
    Gruner, Daniel S.
    [J]. JOURNAL OF ECONOMIC ENTOMOLOGY, 2022, 115 (01) : 381 - 386
  • [2] Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin
    Antonsen, Simen G.
    Gallantree-Smith, Harrison
    Gorbitz, Carl Henrik
    Hansen, Trond Vidar
    Stenstrom, Yngve H.
    Nolsoe, Jens M. J.
    [J]. MOLECULES, 2017, 22 (10)
  • [3] Progress in the classical biological control of Agrilus planipennis Fairmaire (Coleoptera: Buprestidae) in North America
    Bauer, Leah S.
    Duan, Jian J.
    Gould, Juli R.
    Van Driesche, Roy
    [J]. CANADIAN ENTOMOLOGIST, 2015, 147 (03) : 300 - 317
  • [4] Isolation and determination of absolute configurations of insect-produced methyl-branched hydrocarbons
    Bello, Jan E.
    McElfresh, J. Steven
    Millar, Jocelyn G.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2015, 112 (04) : 1077 - 1082
  • [5] Clarification of the Stereochemical Course of Nucleophilic Substitution of Arylsulfonate-Based Nucleophile Assisting Leaving Groups
    Braddock, D. Christopher
    Pouwer, Rebecca H.
    Burton, Jonathan W.
    Broadwith, Phillip
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) : 6042 - 6049
  • [6] Cappaert David, 2005, American Entomologist, V51, P152
  • [7] Effects of emamectin benzoate trunk injections on protection of neighboring ash trees against emerald ash borer (Coleoptera: Buprestidae) and on established biological control agents
    Duan, Jian J.
    Crandall, Ryan S.
    Grosman, Donald M.
    Schmude, Jonathan M.
    Quinn, Nicole
    Chandler, Jennifer L.
    Elkinton, Joseph S.
    [J]. JOURNAL OF ECONOMIC ENTOMOLOGY, 2023, 116 (03) : 848 - 854
  • [8] Impacts of the emerald ash borer (Agrilus planipennis Fairmaire) induced ash (Fraxinus spp.) mortality on forest carbon cycling and successional dynamics in the eastern United States
    Flower, Charles E.
    Knight, Kathleen S.
    Gonzalez-Meler, Miquel A.
    [J]. BIOLOGICAL INVASIONS, 2013, 15 (04) : 931 - 944
  • [9] Mortality of Bark- and Wood-boring Beetles (Coleoptera: Buprestidae, Cerambycidae, and Curculionidae) in Naturally Infested Heat-treated Ash, Birch, Oak, and Pine Bolts
    Haack, Robert A.
    Petrice, Toby R.
    [J]. JOURNAL OF ECONOMIC ENTOMOLOGY, 2022, 115 (06) : 1964 - 1975
  • [10] Asymmetric Total Synthesis of Mycobacterial Diacyl Trehaloses Demonstrates a Role for Lipid Structure in Immunogenicity
    Holzheimer, Mira
    Reijneveld, Josephine F.
    Ramnarine, Alexandrea K.
    Misiakos, Georgios
    Young, David C.
    Ishikawa, Eri
    Cheng, Tan-Yun
    Yamasaki, Sho
    Moody, D. Branch
    Van Rhijn, Ildiko
    Minnaard, Adriaan J.
    [J]. ACS CHEMICAL BIOLOGY, 2020, 15 (07) : 1835 - 1841
123