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Gries, Gerhard; Clearwater, J. R.; Khaskin, Grigori; King, Skip; Schaefer, Paul W.

doi:10.1023/a:1020833909739

Cited by 11 publications

(4 citation statements)

References 9 publications

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“…The abbreviations in Table 4 are made with respect to the acid moiety. Unsaturated ketones with a C 19 -C 21 chain have been identified from two species in Carposinidae (Copromorphoidea) [86,87], one species in Geometridae [88], and five species in Lymantriidae [89][90][91][92][93][94]. Their chemical structures have been abbreviated corresponding to the Type II pheromones without a terminal functional group, and supplying 'ket' to indicate the position of the carbonyl group.…”

Section: Structures Of Other Female Pheromonesmentioning

confidence: 99%

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Lepidopteran Sex Pheromones

Ando

Inomata

Yamamoto

2004

Topics in Current Chemistry

339

289

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As a consequence of the diversity of Lepidoptera, including 150,000 described species, interesting species-specific sex pheromone systems are exhibited in this insect group. The quite varied pheromones, which have been identified from female moths of nearly 530 species from around the world, are classified into groups of Type I (75%), Type II (15%), and miscellaneous (10%), according to their chemical structures. Additionally, many pheromones produced by male moths and butterflies have been known. While new sex pheromones from about 70 lepidopteran species have been reported in the last five years utilizing GC-EAD, GC-MS, LC, and NMR, our information about the pheromones is still rudimentary, and these kinds of semiochemicals remain an exciting research target for natural product chemistry. In addition to the overview of their chemical structures, this chapter deals with current methods for their identification. Furthermore, an actual application of the synthetic pheromones for pest control is briefly introduced.

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Section: Structures Of Other Female Pheromonesmentioning

confidence: 99%

“…Recently, this problem was resolved by the introduction of a dispenser that included the four-component blend [188]. 90 T. Ando et al…”

Section: Applications Of Synthetic Pheromones For Pest Controlmentioning

confidence: 99%

Lepidopteran Sex Pheromones

Ando

Inomata

Yamamoto

2004

Topics in Current Chemistry

339

289

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“…Compounds of general formula 6 – 11 , with R=alkyl or aryl, R′=H or Me, and R′′=H or Me occur in the literature as key intermediates for the synthesis of natural products, pheromones, cosmetics and drugs . Their known syntheses typically involve the chemistry of terminal alkynes according to the following procedures: (i) coupling of terminal alkynes with acrolein in the presence of Pd(OAc) 2 and PMe 3 ; (ii) coupling of terminal alkynols with aryl bromides using CuI and Pd(PPh 3 ) 2 Cl 2 ; (iii) reaction of the lithium salt of terminal alkynes with allyl bromide (followed by hydroboration of the C=C double bond) or with O ‐protected bromoalkanols; (iv) Corey‐Fuchs conversion of aldehydes into terminal alkynes, followed by chain elongation with BuLi and alkyl halides;– (v) Smiles rearrangement of sulfone derivatives, obtained by conjugate addition of keto heterocyclic sulfones to unsaturated aldehydes …”

Section: Resultsmentioning

confidence: 99%

Chemoselective Biohydrogenation of Alkenes in the Presence of Alkynes for the Homologation of 2‐Alkynals/3‐Alkyn‐2‐ones into 4‐Alkynals/Alkynols

et al. 2019

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The chemoselective hydrogenation of alkenes in the presence of alkynes is a very challenging transformation to achieve with traditional chemical methods. The development of an effective procedure to perform this transformation would enrich the tool-kit available to organic chemists for the development of useful synthetic routes, and the creation of novel structural motifs. The reduction of activated alkene bonds by ene-reductases (ERs) is completely chemoselective, because of the mechanism of the reaction. Thus, we investigated the use of ERs belonging to the Old Yellow Enzyme family for the reduction of α,β-unsaturated aldehydes with a conjugated C�C triple bond at the γ position. This reaction was exploited as the key step for the development of an effective homologation route to convert aryl and alkyl substituted propynals and butynones into 4-alkynals and 4-alkynols, avoiding some troublesome or hazardous steps of known synthetic routes. Scheme 4. Conversion of aldehydes (R)-8 a, b and alcohols (S)-10 a, b into derivatives of known absolute configuration.

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“…Use of 2 equiv of base to deprotonate both the alcohol and terminal alkyne in 16, and HMPA as the solvent in the nucleophilic substitution, allowed the reaction to proceed without protection of the primary alcohol. 32 Subsequent hydrogenation of the alkyne in the substitution product 18 provided alcohol 19, which was transformed into bromide 20 by treatment with CBr 4 /PPh 3 . One-carbon homologation 33 proceeded efficiently on heating a solution of bromide 20 with Na 14 C N in DMSO at 85°C to provide nitrile 21.…”

Section: Synthesis Of 14 C -Labelled Threitol Ceramidementioning

confidence: 99%