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 24 条
[21]   DIASTEREOSELECTIVE [2,3]-WITTIG REARRANGEMENT OF A TERTIARY BISALLYLIC ETHER [J].
SHI, XW ;
WEBSTER, FX ;
KALLMERTEN, J ;
MEINWALD, J .
TETRAHEDRON LETTERS, 1995, 36 (40) :7197-7200
[22]   SYNTHESES OF THE FEMALE SEX-PHEROMONES OF MATSUCOCCUS PINE SCALES USING THE [2,3]-WITTIG REARRANGEMENT OF A BISALLYLIC TERTIARY ETHER [J].
SHI, XW ;
WEBSTER, FX ;
MEINWALD, J .
TETRAHEDRON, 1995, 51 (38) :10433-10442
[23]   IDENTIFICATION OF THE AGGREGATION PHEROMONE OF FLOUR BEETLES TRIBOLIUM-CASTANEUM AND TRIBOLIUM-CONFUSUM (COLEOPTERA, TENEBRIONIDAE) [J].
SUZUKI, T .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1981, 45 (06) :1357-1363
[24]   SYNTHESIS AND FIELD BIOASSAY OF THE ISRAELI PINE BAST SCALE, MATSUCOCCUS-JOSEPHI, FEMALE SEX-PHEROMONE [J].
ZEGELMAN, L ;
HASSNER, A ;
MENDEL, Z ;
DUNKELBLUM, E .
TETRAHEDRON LETTERS, 1993, 34 (35) :5641-5644