Asymmetric synthesis of (–)-dehydro-exo-brevicomin with photoisomerisation–intramolecular acetalisation sequence

2021 ◽  
Author(s):  
Shun Hirasawa ◽  
Tsuyoshi Masuda ◽  
Ken Mukai ◽  
Yusuke Miyoshi ◽  
Nobuhiro Kanomata
Keyword(s):  
Sex Pheromone ◽  
Asymmetric Synthesis ◽  
House Mice

We herein reported a novel, short asymmetric synthesis of (–)-dehydro-exo-brevicomin (DHB, 1), a sex pheromone isolated from house mice, in 44% overall yield, the highest yield reported so far, over...

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

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

Asymmetric synthesis of a sex pheromone (3S,5R,6S)-3,5-dimethyl-6-isopropyl-3,4,5,6-tetrahydropyran-2-one

2009 ◽  
Vol 20 (15) ◽  
pp. 1806-1808 ◽  
Author(s):  
Peddikotla Prabhakar ◽  
Singanaboina Rajaram ◽  
Yenamandra Venkateswarlu
Keyword(s):  
Sex Pheromone ◽  
Asymmetric Synthesis

Asymmetric synthesis of (2R,5S)-2-methyl-5-hexanolide, the sex pheromone of carpenter bee Xylocopa hirutissima

2008 ◽  
Vol 19 (18) ◽  
pp. 2164-2166 ◽  
Author(s):  
Jian-Hong Yang ◽  
Gui-Chun Yang ◽  
Cui-Fen Lu ◽  
Zu-Xing Chen
Keyword(s):  
Sex Pheromone ◽  
Asymmetric Synthesis ◽  
Carpenter Bee

An ephemeral sex pheromone in the urine of female house mice (Mus domesticus)

1992 ◽  
Vol 58 (2) ◽  
pp. 138-143 ◽  
Author(s):  
Maurice L. Sipos ◽  
Michael Kerchner ◽  
John G. Nyby
Keyword(s):  
Sex Pheromone ◽  
House Mice ◽  
Mus Domesticus

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
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