Facile Synthesis of Mill Moth's Sex Pheromone Components

Hornyánszky, Gábor; Rohaly, J.; Novák, Lajos

doi:10.1080/00397910801929341

Cited by 8 publications

(4 citation statements)

References 13 publications

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“…6-(4-Methoxyphenylmethoxy)-1-hexanal and ( E )-3-penten-1-ol were prepared following the procedures reported in literature.…”

Section: Methodsmentioning

confidence: 99%

“…Column chromatography of the crude material using 30% AgNO 3 /silica gel afforded 363 mg of silyl ether 1j (43% yield over 2 steps) as a colorless oil. IR (neat): 3077 w, 2924 s, 2854 s, 2721 w, 1823 w, 1642 w, 1464 s, 1382 w, 1367 w, 1248 w, 1107 s, 1070 m, 1014 m, 995 m, 909 m, 883 s, 791 w, 721 w, 681 s, 658 m, 640 m cm −1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 0.99−1.15 (m, 21H), 1.21−1.39 (m, 30H), 1.50−1.57 (m, 2H), 2.04 (q, J = 7.2 Hz, 2H), 3.66 (t, J = 6.8 Hz, 2H), 4.91−5.02 (m, 2H), 5.76−5.87 (m, 1H); 13 22 and (E)-3-penten-1-ol 23 were prepared following the procedures reported in literature.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking

et al. 2018

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Selective long-distance isomerization of terminal alkenes to silyl enol ethers proceeded via nondissociative chain walking using phenanthroline palladium catalysts. Notable features achieved taking advantage of the nondissociative chain walking mechanism include high efficiency obtained regardless of the chain length, high chemoselectivity toward terminal alkenes over internal ones, and retention of the stereoconfiguration of the stereocenter on the alkyl chain.

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“…6-(4-Methoxyphenylmethoxy)-1-hexanal and ( E )-3-penten-1-ol were prepared following the procedures reported in literature.…”

Section: Methodsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking

et al. 2018

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“…The use of GZ-2 simplified the route to 112 to just two steps instead of the formerly reported six steps (Scheme ). , …”

Section: Pheromone Synthesis Via Cross-metathesismentioning

confidence: 99%

“…The use of GZ-2 simplified the route to 112 to just two steps instead of the formerly reported six steps (Scheme 29). 73,74 Further catalyst development led to the identification of GZ-3 (see Scheme 25 for the structure), 75 a catalyst that enables the synthesis of conjugated (E,Z)-dienes. GZ-3 does not react and isomerize E double bonds, making possible the synthesis of conjugated (E,Z)-dienes.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Semiochemicals via Olefin Metathesis

Turczel

Kovács

Merza

et al. 2018

ACS Sustainable Chem. Eng.

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Semiochemicals are substances or mixtures that carry messages and are used for communication between individuals of the same or different species. Semiochemicals that are used in pest control are called biopesticides. Conventional pesticides, which are generally synthetically derived and unnatural, inactivate or kill the pests, whereas biopesticides are naturally occurring compounds that attract insects to a trap or interfere with their reproduction.There are several advantages to biopesticides. Compared to conventional pesticides, biochemical-based pesticides are often less toxic and therefore pose a significantly lower impact 2 on human health and the environment. Moreover, the biopesticides are pest selective and as such, do not negatively impact other organisms such as insects, mammals or birds. Other advantages of biopesticides include high potency, meaning that smaller amounts of biopesticide are required, less resistance by target organisms, and the ability to biodegrade more quickly than conventional pesticides. [1][2][3] Although the biochemical-based pesticides are very promising materials, their production is often cumbersome and their application is often limited. So far, most of the biopesticides are synthesized by multistep, classical organic reactions which are not economical and pose high environmental impact. However, in recent decades, many efforts have been done to implement cost-effective and safer chemical procedures for the widespread application of biochemical-based pesticides. The purpose of this perspective is to draw the attention of the green chemistry community to the applicability of olefin metathesis reactions in environmental benign and cost-effective biopesticide synthesis. In this article, we review seminal work on the total synthesis of biopesticides using olefin metathesis as a key reaction step, and in doing so, we hope to inspire new ideas for forthcoming olefin metathesis based biopesticide development.

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Concise Syntheses of Insect Pheromones Using Z‐Selective Cross Metathesis

et al. 2012

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The shortest synthetic routes to nine cis-pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported. These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z-olefins. Important insight into the mechanism of Z-selective metathesis was uncovered during experimentation and subsequently explored. KeywordsZ-olefin; insect pheromone; olefin metathesis; seed oil derivatives; unconjugated diene The use of insect sex pheromones to limit specifically targeted pest populations has gained increasing popularity as a viable, safe, and environmentally-friendly alternative to insecticides. While broad spectrum insecticides are toxic compounds that have been shown to adversely affect human health, [1] extensive studies have revealed that insect pheromones are nontoxic and safe for human consumption at the levels used in pest control practices. [2] Female sex pheromones are mainly employed in pest control in a process termed mating

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Facile Synthesis of Mill Moth's Sex Pheromone Components

Abstract: An improved method for the preparation of mill moth's sex pheromone components in high diastereomeric purity is described.

Cited by 8 publications

References 13 publications

Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking

Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking

Synthesis of Semiochemicals via Olefin Metathesis

Concise Syntheses of Insect Pheromones Using Z‐Selective Cross Metathesis

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