Concise synthesis of a racemic and diastereomeric mixture of the sex pheromones of Matsucoccus pine scales

被引:165
|
作者
Watanabe, H [1 ]
Watanabe, T [1 ]
Kitahara, T [1 ]
Mori, K [1 ]
机构
[1] SCI UNIV TOKYO, DEPT CHEM, SHINJUKU KU, TOKYO 162, JAPAN
关键词
sex pheromone; pine scale; Matsucoccus; cyanation of allylic alcohol;
D O I
10.1271/bbb.61.127
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A short (3-5 steps) synthesis of a racemic and diastereomeric mixture of Matsucoccucs sex pheromones (1-3) is described. The key reaction is Lewis acid-mediated cyanation of symmetric tertiary alcohol 6 to afford common intermediate 7.
引用
收藏
页码:127 / 130
页数:4
相关论文
共 36 条
  • [1] A concise synthesis of the sex pheromones of Pine sawflies
    Wang, Zi-Kun
    Tian, Wei-Sheng
    Pan, Xin-Fu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2007, 27 (07) : 866 - 869
  • [2] SYNTHESIS OF MATSUCOCCUS PINE SCALE PHEROMONES - ASSIGNMENT OF RELATIVE AND ABSOLUTE STEREOCHEMISTRY
    CYWIN, CL
    KALLMERTEN, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 137 - ORGN
  • [3] IDENTIFICATION OF THE SEX-PHEROMONE OF 3 MATSUCOCCUS PINE BAST SCALES
    LANIER, GN
    QI, YT
    WEST, JR
    PARK, SC
    WEBSTER, FX
    SILVERSTEIN, RM
    JOURNAL OF CHEMICAL ECOLOGY, 1989, 15 (05) : 1645 - 1659
  • [4] SYNTHESIS AND THE DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF MATSUONE, SEX-PHEROMONE OF FEMALE MATSUCOCCUS PINE SCALES
    SHI, XW
    WEBSTER, FX
    MEINWALD, J
    TETRAHEDRON LETTERS, 1995, 36 (40) : 7201 - 7204
  • [5] SYNTHESES OF THE FEMALE SEX-PHEROMONES OF MATSUCOCCUS PINE SCALES USING THE [2,3]-WITTIG REARRANGEMENT OF A BISALLYLIC TERTIARY ETHER
    SHI, XW
    WEBSTER, FX
    MEINWALD, J
    TETRAHEDRON, 1995, 51 (38) : 10433 - 10442
  • [6] Synthesis of the C(7)∼C(13) fragment of Matsuone, a sex pheromone of the Matsucoccus pine bast scales
    Huang, Xian-Gui
    Li, Tao
    Lin, Jing-Rong
    Jin, Rong-Hua
    Tian, Wei-Sheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2007, 27 (03) : 428 - 430
  • [7] Synthesis and structure-activity relationship of diene modified analogs of Matsucoccus sex pheromones
    Mendel, Z
    Dunkelblum, E
    Branco, M
    Franco, JC
    Kurosawa, S
    Mori, K
    NATURWISSENSCHAFTEN, 2003, 90 (07) : 313 - 317
  • [8] Synthesis and structure-activity relationship of diene modified analogs of Matsucoccus sex pheromones
    Z. Mendel
    E. Dunkelblum
    M. Branco
    J. C. Franco
    S. Kurosawa
    K. Mori
    Naturwissenschaften, 2003, 90 : 313 - 317
  • [9] ENANTIOSELECTIVE SYNTHESIS OF A SEX ATTRACTANT PHEROMONE OF THE PINE SCALE MATSUCOCCUS-FEYTAUDI
    CYWIN, CL
    KALLMERTEN, J
    JOURNAL OF NATURAL PRODUCTS, 1991, 54 (06): : 1664 - 1667
  • [10] LABORATORY AND FIELD-TESTS WITH THE SYNTHETIC SEX-PHEROMONE OF 3 MATSUCOCCUS PINE BAST SCALES
    HIBBARD, BE
    LANIER, GN
    PARKS, SC
    QI, YT
    WEBSTER, FX
    SILVERSTEIN, RM
    JOURNAL OF CHEMICAL ECOLOGY, 1991, 17 (01) : 89 - 102