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

来源：

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 1997年 / 61卷 / 01期

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

页码：127 / 130

页数：4

共 36 条

[31] Stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-ol and its propionate, the sex pheromones of pine sawflies
Kovalenko, Vitaly
Matiushenkov, Evgenii
TETRAHEDRON-ASYMMETRY, 2012, 23 (18-19) : 1393 - 1399
[32] 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
LIN, GQ
XU, WC
TETRAHEDRON LETTERS, 1993, 34 (37) : 5931 - 5934
[33] Enzymatic synthesis of (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale
Lin, GQ
Xu, WC
BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (03) : 375 - 380
[34] Synthesis and bioassay of all four stereoisomers of (2E,4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the assignment of the absolute configuration of the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale
LIN
Chinese Journal of Chemistry, 1995, (01) : 85 - 94
[35] SYNTHESIS OF (2E,4E,6R,10S)-4,6,10-TRIMETHYL-2,4-DODECADIEN-7-ONE - THE MAJOR COMPONENT OF THE SEX-PHEROMONE OF THE MARITIME PINE SCALE (MATSUCOCCUS-FEYTAUDI) - AND ITS 3 STEREOISOMERS
MORI, K
HARASHIMA, S
LIEBIGS ANNALEN DER CHEMIE, 1993, (04): : 391 - 401
[36] Practical synthesis of the main sex pheromones of pine sawflies (2S,3S,7S)-3,7-dimethylpentadecan-2-ol esters by utilizing (R)-4-methyl-δ-valerolactone obtained from the industrial waste
Wang Zi-Kun
Tian Wei-Sheng
Pan Xin-Fu
ACTA CHIMICA SINICA, 2007, 65 (08) : 705 - 710

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