scholarly journals Selective alkylation of diethyl 3-oxoglutarate. Part VII. Convenient synthesis of muscalure, the housefly sex pheromone.

1981 ◽  
Vol 45 (7) ◽  
pp. 1723-1724 ◽  
Author(s):  
Yoshinobu NAOSHIMA ◽  
Hiroshi OZAWA ◽  
Yasuyuki TAKENAMI ◽  
Shoji WAKABAYASHI ◽  
Shuichi HAYASHI
Keyword(s):  
Sex Pheromone ◽  
Convenient Synthesis ◽  
Selective Alkylation

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.

scholarly journals Selective alkylation of ethyl 3-oxoglutarate. Part V. A facile synthesis of 2-methylheptadecane, sex pheromone of tiger moths (Arctiidae)

1980 ◽  
Vol 44 (9) ◽  
pp. 2231-2232 ◽  
Author(s):  
Yoshinobu NAOSHIMA ◽  
Takao YAMAMOTO ◽  
Shoji WAKABAYASHI ◽  
Shûichi HAYASHI
Keyword(s):  
Sex Pheromone ◽  
Facile Synthesis ◽  
Selective Alkylation ◽  
Tiger Moths

A Convenient Synthesis of (Z)-6-Heneicosen-11-one — A Sex Pheromone of the Douglas-Fir Tussock Moth

1983 ◽  
Vol 13 (5) ◽  
pp. 379-385 ◽  
Author(s):  
P. Satyanarayana Reddy ◽  
A. B. Sahasrabudhe ◽  
J. S. Yadav
Keyword(s):  
Sex Pheromone ◽  
Douglas Fir ◽  
Tussock Moth ◽  
Convenient Synthesis

Convenient Synthesis of Muscalure, the Housefly Sex Pheromone

1981 ◽  
Vol 45 (7) ◽  
pp. 1723-1724 ◽  
Author(s):  
Yoshinobu Naoshima ◽  
Hiroshi Ozawa ◽  
Yasuyuki Takenami ◽  
Shoji Wakabayashi ◽  
Shûichi Hayashi
Keyword(s):  
Sex Pheromone ◽  
Convenient Synthesis

A convenient synthesis of 2,13- and 3,13-octadecadienyl acetates, sex pheromone components of the Synanthedon species

1990 ◽  
Vol 55 (9) ◽  
pp. 2270-2281 ◽  
Author(s):  
Michal Hoskovec ◽  
David Šaman ◽  
Bohumír Koutek
Keyword(s):  
Sex Pheromone ◽  
Triple Bond ◽  
Chain Elongation ◽  
Ni Catalyst ◽  
Nmr Data ◽  
Sex Pheromone Components ◽  
Convenient Synthesis ◽  
Pheromone Components ◽  
C Nmr

The sex pheromone components of several Synanthedon species, 2,13- and 3,13-octadecadienyl acetates (Ic, Id, IIc, IId), have been synthesized following the acetylenic route of chain elongation. Starting from ω-alkyn-1-ols III, the final compounds were constructed in five steps in about 30% overall yields. Transformation of triple bond containing intermediates into the corresponding (Z)- and (E)-olefins was achieved either by hydrogenation over the P2-Ni catalyst or by using a dispersion of sodium in toluene. The title pheromones were generated in more than 97% stereoisomeric purity. 1H and 13C NMR data of all derivatives are included.

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