Synthesis of the sex pheromone of the grain moth Ephestia elutella

Kasymzhanova, M. M.; Abdukakharov, V. S.; Камаев, Ф. Г.; Abduvakhabov, A. A.

doi:10.1007/bf00598272

Cited by 4 publications

(4 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1-tert-Butoxy-dec-9-yne (6) All operations were performed in an inert gas atmosphere and under stirring. To a stirred and cooled (0°C) suspension of 3.8 g (41.30 mmoles) lithium acetylide-ethylendiamine complex (5) in 20.65 mL anhydrous dimethyl sulfoxide was added 5.47 g (20.64 mmoles) of 1-tert-butoxy-8-bromo-octan (4).…”

Section: -Bromo-1-octanol (3)mentioning

confidence: 99%

“…The synthesis of (9Z,12E)-9,12-tetradecadiene-1-yl acetate is well known in the literature [2][3][4][5][6][7][8][9][10]. The pheromone has been prepared by the Wittig reaction [11], Grignard reagent reaction with allyl bromide in the presence of copper (I) salts [12], Wittig condensation between triphenyl-phosphonium (E)-3-pentenylide and 9-acetoxy-1-nonanal using either potassium in HMPT [13], cross-coupling reaction [14], coupling 2-(8-chloro-1-octyloxy)tetrahydropyran with lithium acetylide followed by reaction of lithium salt with (E)-1-bromo-2-butene [15].…”

mentioning

confidence: 99%

See 1 more Smart Citation

A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae)

Andreica¹,

Gansca²,

Ciotlaus³

et al. 2020

Rev. Chim.

View full text Add to dashboard Cite

New synthesis of (9Z,12E)-9,12-tetradecadien-1-yl acetate, the sex pheromone of the indian meal moth Plodia interpunctella (Lepidoptera, Pyralidae), were developed. The synthesis was based on a C8+C2=C10 and C10+C4=C14 coupling scheme. The route involves, as the key step, the use of the mercury derivative of the terminal-alkyne -functionalised as intermediate.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.In the second coupling reaction, the mercury derivative was directly lithiated and then alkylated with (E)-1-bromo-2-butene obtaining 1-tert-butoxy-(9-yne,12E)-9,12-tetradecaenyne. After stereoselective reduction in the presence of NiP-2 catalyst and acetylation gave (9Z,12E)-9,12-tetradecadien-1-yl acetate with 82% isomeric purity.

show abstract

Section: -Bromo-1-octanol (3)mentioning

confidence: 99%

mentioning

confidence: 99%

A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae)

Andreica¹,

Gansca²,

Ciotlaus³

et al. 2020

Rev. Chim.

View full text Add to dashboard Cite

show abstract

“…3H, s, CH 3 ), 2.42 (2H, t, J ¼ 7.1 Hz, CH 2 ), 4.05 (2H, t, J ¼ 6.8 Hz, OCH 2 ), 9.76 (1H, s, CHO) 13. C NMR (CDCl 3 ): 20.94 (CH 3 ), 21.98 (CH 2 ), 25.77 (CH 2 ), 28.50 (CH 2 ), 28.98 (CH 2 ), 29.08 (CH 2 ), 29.29 (CH 2 ), 43.76 (CH 2 ), 64.38 (OCH 2 ), 170.74 (CO), 202.20 (CHO).…”

mentioning

confidence: 99%

“…2H, t, J ¼ 6.6 Hz, OCH 2 ), 5.39 (4H, m, 4CH5 5) 13. C NMR (CDCl 3 ): 18.27 (CH 3 ), 26.09 (CH 2 ), 27.44 (CH 2 ), 29.55 (CH 2 ), 29.74 (CH 2 ), 29.82 (CH 2 ), 29.98 (CH 2 ), 30.78 (CH 2 ), 33.14 (CH 2 ), 63.32 (OCH 2 ), 125.15 (CH5 5), 127.73 (CH5 5), 129.68 (CH5 5), 130.45 (CH5 5).…”

mentioning

confidence: 99%