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

被引：12
|
作者：
Sun, Zhi-Feng [1 ,2 ]
Zhou, Lu-Nan [1 ]
Meng, Yifei [1 ]
Zhang, Tao [1 ]
Du, Zhen-Ting [1 ]
Zheng, Huaiji [1 ]
机构：
[1] North West Agr & Forestry Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, Yangling 712100, Shaanxi, Peoples R China
[2] Shaanxi Univ Technol, Coll Chem & Environm Sci, Shaanxi Key Lab Catalysis, Hanzhong 723001, Shaanxi, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2017年 / 28卷 / 11期
基金：
中国国家自然科学基金;
关键词：
EUPROCTIS-PSEUDOCONSPERSA STRAND; JULIA OLEFINATION; LYMANTRIIDAE; LEPIDOPTERA; ISOBUTYRATE; RESPONSES; PRODUCT;
D O I：
10.1016/j.tetasy.2017.09.007
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
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 C-C 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. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1562 / 1567
页数：6
相关论文
共 50 条
  • [41] Responses of Tea Tussock Moth, Euproctis pseudoconspersa, to Its Pheromone, (R)-10,14-Dimethylpentadecyl Isobutyrate, and to the S-Enantiomer of Its Pheromone
    Cheng-Hua Zhao
    Jocelyn G. Millar
    Kun-Hui Pan
    Cai-Sheng Xu
    Journal of Chemical Ecology, 1998, 24 : 1347 - 1353
  • [42] A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth
    Liang Wei
    Guo-Guo He
    Lu Liu
    Meng Tang
    Tao Zhang
    Hongjin Bai
    Zhen-Ting Du
    Russian Journal of Organic Chemistry, 2020, 56 : 1089 - 1095
  • [43] A Facile Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth
    Zhang, Tao
    Ma, Wei-Li
    Li, Tian-Rui
    Wu, Jia
    Wang, Jun-Run
    Du, Zhen-Ting
    MOLECULES, 2013, 18 (05) : 5201 - 5208
  • [44] A New Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth
    He, Guo-Guo
    Liu, Si-Fan
    Rao, Bao-Qi
    Bai, Hong-Jin
    Du, Zhen-Ting
    NATURAL PRODUCT COMMUNICATIONS, 2021, 16 (05)
  • [45] A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth
    Wei, Liang
    He, Guo-Guo
    Liu, Lu
    Tang, Meng
    Zhang, Tao
    Bai, Hongjin
    Du, Zhen-Ting
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (06) : 1089 - 1095
  • [46] SEX-PHEROMONE OF CODLING MOTH
    MCDONOUGH, LM
    MOFFITT, HR
    SCIENCE, 1974, 183 (4128) : 978 - 978
  • [47] SEX PHEROMONE OF ORIENTAL FRUIT MOTH
    ROELOFS, WL
    COMEAU, A
    SELLE, R
    NATURE, 1969, 224 (5220) : 723 - &
  • [48] Evolution of Moth Sex Pheromone Desaturases
    Rooney, Alejandro R.
    INTERNATIONAL SYMPOSIUM ON OLFACTION AND TASTE, 2009, 1170 : 506 - 510
  • [49] ISOLATION OF A SEX PHEROMONE OF CODLING MOTH
    MCDONOUG.LM
    GEORGE, DA
    BUTT, BA
    JACOBSON, M
    JOHNSON, GR
    JOURNAL OF ECONOMIC ENTOMOLOGY, 1969, 62 (01) : 62 - &
  • [50] Syntheses of the sex pheromone of the Codling moth
    Popovici, N
    REVUE ROUMAINE DE CHIMIE, 1997, 42 (03) : 221 - 224
12345