scholarly journals Synthesis of the Enantiomers of (Z)-5-(1-Octenyl)oxacyclopentan-2-one, a Sex Pheromone of the Cupreous Chafer Beetle,Anomala cupreaHope

1992 ◽  
Vol 56 (7) ◽  
pp. 1160-1161 ◽  
Author(s):  
Eiichiro Fukusaki ◽  
Shuji Senda ◽  
Yutaka Nakazono ◽  
Tetsuo Omata
Keyword(s):  
Sex Pheromone ◽  
Cupreous Chafer

Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean
Keyword(s):  
Sex Pheromone ◽  
Coupling Reaction ◽  
Coupling Scheme ◽  
Lithium Aluminium Hydride ◽  
Terminal Alkyne ◽  
Mercury Derivative ◽  
Lithium Aluminium ◽  
Convenient Synthesis ◽  
Practical Synthesis ◽  
Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

Identification of Sex Pheromone of Miltochrista striata (Lepidoptera: Arctiidae)

2019 ◽  
Vol 112 (2) ◽  
pp. 665-670
Author(s):  
Luo Zongxiu ◽  
Cai Xiaoming ◽  
Li Zhaoqun ◽  
Bian Lei ◽  
Xin Zhaojun ◽  
...  
Keyword(s):  
Sex Pheromone

scholarly journals Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid‐Producing Plants

2021 ◽  
Author(s):  
Suzanne J. Partridge ◽  
David M. Withall ◽  
John C. Caulfield ◽  
John A. Pickett ◽  
Robert A. Stockman ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Pheromone Biosynthesis ◽  
Sex Pheromone Biosynthesis
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