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
[1]   SYNTHESIS OF (-)-(6R,10R)-MATSUONE - ASSIGNMENT OF RELATIVE STEREOCHEMISTRY TO A PHEROMONE OF MATSUCOCCUS PINE BAST SCALES [J].
CYWIN, CL ;
WEBSTER, FX ;
KALLMERTEN, J .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2953-2955
[2]   ENANTIOSELECTIVE SYNTHESIS OF A SEX ATTRACTANT PHEROMONE OF THE PINE SCALE MATSUCOCCUS-FEYTAUDI [J].
CYWIN, CL ;
KALLMERTEN, J .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (06) :1664-1667
[3]   CHIRALITY OF ISRAELI PINE BAST SCALE, MATSUCOCCUS-JOSEPHI (HOMOPTERA, MATSUCOCCIDAE) SEX-PHEROMONE [J].
DUNKELBLUM, E ;
GRIES, R ;
GRIES, G ;
MORI, K ;
MENDEL, Z .
JOURNAL OF CHEMICAL ECOLOGY, 1995, 21 (06) :849-858
[4]   IDENTIFICATION OF THE FEMALE SEX-PHEROMONE OF THE ISRAELI PINE BAST SCALE MATSUCOCCUS-JOSEPHI [J].
DUNKELBLUM, E ;
MENDEL, Z ;
ASSAEL, F ;
HAREL, M ;
KERHOAS, L ;
EINHORN, J .
TETRAHEDRON LETTERS, 1993, 34 (17) :2805-2808
[5]   IDENTIFICATION OF THE SEX-PHEROMONE OF THE MARITIME PINE SCALE MATSUCOCCUS-FEYTAUDI [J].
EINHORN, J ;
MENASSIEU, P ;
MALOSSE, C ;
DUCROT, PH .
TETRAHEDRON LETTERS, 1990, 31 (46) :6633-6636
[6]  
HOSHIAI K, 1959, KOGYO KAGAKU ZASSHI, V62, P686
[7]   FIELD RESPONSE OF MARITIME PINE SCALE, MATSUCOCCUS-FEYTAUDI DUC (HOMOPTERA, MARGARODIDAE), TO SYNTHETIC SEX-PHEROMONE STEREOISOMERS [J].
JACTEL, H ;
MENASSIEU, P ;
LETTERE, M ;
MORI, K ;
EINHORN, J .
JOURNAL OF CHEMICAL ECOLOGY, 1994, 20 (09) :2159-2170
[8]   SYNTHESIS OF 2-SUBSTITUTED DELTA-3-PIPERIDINES - THE NITROGEN ANALOG OF THE FERRIER REARRANGEMENT - AN APPROACH TO STREPTAZOLIN [J].
KOZIKOWSKI, AP ;
PARK, P .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1674-1676
[9]   IDENTIFICATION OF THE SEX-PHEROMONE OF 3 MATSUCOCCUS PINE BAST SCALES [J].
LANIER, GN ;
QI, YT ;
WEST, JR ;
PARK, SC ;
WEBSTER, FX ;
SILVERSTEIN, RM .
JOURNAL OF CHEMICAL ECOLOGY, 1989, 15 (05) :1645-1659
[10]   ENANTIOSELECTIVE SYNTHESIS OF ALL 4 STEREOISOMERS OF (2E,4E)-4,6,10,12-TETRAMETHYL-2,4-TRIDECADIEN-7-ONE, THE SEX-PHEROMONE OF MATSUCOCCUS PINE BAST SCALE [J].
LIN, GQ ;
XU, WC .
TETRAHEDRON LETTERS, 1993, 34 (37) :5931-5934