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

2017 ◽  
Vol 28 (11) ◽  
pp. 1562-1567 ◽  
Author(s):  
Zhi-Feng Sun ◽  
Lu-Nan Zhou ◽  
Yifei Meng ◽  
Tao Zhang ◽  
Zhen-Ting Du ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Asymmetric Synthesis ◽  
Tussock Moth

Identification Of Sex Pheromone Components Of The Painted Apple Moth: A Tussock Moth With A Thermally Labile Pheromone Component

2005 ◽  
Vol 31 (3) ◽  
pp. 621-646 ◽  
Author(s):  
A. M. El-Sayed ◽  
A. R. Gibb ◽  
D. M. Suckling ◽  
B. Bunn ◽  
S. Fielder ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Pheromone Component ◽  
Tussock Moth ◽  
Sex Pheromone Components ◽  
Pheromone Components

scholarly journals Synthesis of the Sex Pheromone of the Tea Tussock Moth Based on a Resource Chemistry Strategy

Molecules ◽  
2018 ◽  
Vol 23 (6) ◽  
pp. 1347 ◽  
Author(s):  
Hong-Li Zhang ◽  
Zhi-Feng Sun ◽  
Lu-Nan Zhou ◽  
Lu Liu ◽  
Tao Zhang ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Tussock Moth

A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth

2020 ◽  
Vol 56 (6) ◽  
pp. 1089-1095
Author(s):  
Liang Wei ◽  
Guo-Guo He ◽  
Lu Liu ◽  
Meng Tang ◽  
Tao Zhang ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Asymmetric Synthesis

Posticlure: a novel trans-epoxide as a sex pheromone component of the tussock moth, Orgyia postica (Walker)

2001 ◽  
Vol 42 (4) ◽  
pp. 687-689 ◽  
Author(s):  
Sadao Wakamura ◽  
Norio Arakaki ◽  
Masanobu Yamamoto ◽  
Syuntaro Hiradate ◽  
Hiroe Yasui ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Pheromone Component ◽  
Tussock Moth

Asymmetric synthesis towards (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the California red scale pheromone

1985 ◽  
Vol 63 (11) ◽  
pp. 2844-2852 ◽  
Author(s):  
Mark Whittaker ◽  
Colin R. McArthur ◽  
Clifford C. Leznoff
Keyword(s):  
Sex Pheromone ◽  
Asymmetric Synthesis ◽  
Acid Hydrolysis ◽  
Base Hydrolysis ◽  
Addition Reactions ◽  
Tert Butyl ◽  
Mild Hydrolysis

The key chiral synthons, (R)-3-isopropenyl-6-heptenoic acid and (R)-3-isopropenyl-6-heptenal, needed for the synthesis of (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the sex pheromone of the California red scale, Aonidiellaaurantii, have been prepared by asymmetric synthesis. The chiral acid was synthesized in 86% ee by an asymmetric 1,4-addition of isopropenylmagnesium bromide to the l-ephedrine amide derived from (E)-2,6-heptadienoic acid, followed by base hydrolysis. Acid hydrolysis gave the chiral 3-(3-buten-1-yl)-4,4-dimethylbutyrolactone. The chiral aldehyde was prepared in greater than 99% ee by an asymmetric 1,4-addition of isopropenylmagnesium bromide to the imine derived from (S)-(+)-tert-butyl 2-amino-3,3-dimethylbutyrate and (E)-2,6-heptadienal. The 1,4-addition reactions of n-butyllithium or isopropenyllithium to (4S,5S)-(+)-2-[1-(E-1,5-hexadienyl)]-4-methoxymethyl-5-phenyl-2-oxazoline gave the addition products, and sequential mild hydrolysis and reduction of these adducts yielded chiral 3-n-butyl-6-hepten-1-ol for the former adduct but a mixture of products was obtained from the latter adduct.

scholarly journals Asymmetric Synthesis of (3Z,6Z,9S,10R)-9,10-Epoxy-3,6-heneicosadiene, Sex Pheromone Component of Hyphantria cunea

2021 ◽  
Vol 41 (11) ◽  
pp. 4437
Author(s):  
Gucheng Yuan ◽  
Jiawei Liu ◽  
Shihang Yu ◽  
Chaonan Yuan ◽  
Qinghua Bian ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Asymmetric Synthesis ◽  
Pheromone Component ◽  
Hyphantria Cunea
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