During field screening trials of a number of known cerambycid pheromones in China, males of Megopis costipennis (White) (Coleoptera: Cerambycidae: Prioninae: Callipogonini) were found to be specifically attracted to racemic anti-2,3-octanediol, suggesting that one of the enantiomers of this compound might be a female-produced sex pheromone of this species. Analysis of volatiles produced by beetles of both sexes confirmed this hypothesis: females produced (2R,3S)-2,3-octanediol, whereas males did not, and in coupled gas chromatography–electroantennogram detection analyses, antennae from male beetles responded strongly to this compound. In field trials, males were equally attracted to traps baited with either (2R,3S)-2,3-octanediol or racemic anti-2,3-octanediol, indicating that the enantiomeric (2S,3R)-2,3-octanediol does not antagonize attraction to the naturally produced enantiomer. Thus, the more economical racemic anti-2,3-octanediol can be used for trap baits for this species. Homologous 2,3-hexanediols previously had been identified as sex pheromones or sex attractants of prionine species in the genus Tragosoma Audinet-Serville of the tribe Meroscelisini.
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http://dx.doi.org/10.1093/ee/nvv176 | DOI Listing |
Chem Soc Rev
January 2025
Pingyuan Laboratory, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, Henan, P. R. China.
The use of olefins in the construction of cyclic compounds represents a powerful strategy for advancing the pharmaceutical industry. Photocycloaddition has attracted significant interest from chemists due to its ability to exploit simple and readily available olefins along with their reaction patterns under mild conditions. Moreover, the sustainable and versatile pathways for generating highly reactive intermediates can greatly enrich both substrate diversity and reaction patterns.
View Article and Find Full Text PDFJ Org Chem
January 2025
Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Komatsushima 4-4-1, Aoba-ku, Sendai 981-8558, Japan.
Nucleoside derivatives having a 4-substituent show promise as potential antiviral agents as well as nucleoside units for constructing nucleic acid medicines. To develop new nucleosides, it is crucial to achieve feasible access to the intended derivatives, encompassing both enantiomers. Toward this end, we started synthesizing an achiral 4-hydroxymethyldihydrofuran as a sugar precursor, which we subjected to the oxidative glycosylation reaction using hypervalent iodine.
View Article and Find Full Text PDFMolecules
January 2025
Department of Chemistry, National and Kapodistrian University of Athens, 15771 Athens, Greece.
Fatty Acid Esters of Hydroxy Fatty Acids (FAHFAs) have emerged as extraordinary bioactive lipids, exhibiting diverse bioactivities, from the enhancement of insulin secretion and the optimization of blood glucose absorption to anti-inflammatory effects. The intricate nature of FAHFAs' structure reflects a synthetic challenge that requires the strategic introduction of ester bonds along the hydroxy fatty acid chain. Our research seeks to create an effective methodology for generating varied FAHFA derivatives.
View Article and Find Full Text PDFActa Crystallogr C Struct Chem
February 2025
Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
In this study, we present a new N-derivative of L-phenylalanine with 2-naphthaldehyde (PN), obtained by the Schiff base formation procedure and its subsequent reduction. This compound was crystallized as a zwitterion {2-[(naphthalen-2-ylmethyl)azaniumyl]-3-phenylpropanoate, CHNO}, as an anion in a sodium salt (catena-poly[[diaquasodium(I)-di-μ-aqua] 2-[(naphthalen-2-ylmethyl)amino]-3-phenylpropanoate monohydrate], {[Na(HO)](CHNO)·HO}), as a cation in a chloride salt [(1-carboxy-2-phenylethyl)(naphthalen-2-ylmethyl)azanium chloride acetic acid monosolvate, CHNO·Cl·CHCOOH], and additionally acting as a ligand in the pentacoordinated zinc compound aquabis{2-[(naphthalen-2-ylmethyl)amino]-3-phenylpropanoato-κO}zinc(II), [Zn(CHNO)(HO)] or [Zn(PN)(HO)], denoted (PN-Zn), with the amino acid derivative in its carboxylate form.
View Article and Find Full Text PDFChirality
February 2025
Department of Chemistry, Bogazici University, Istanbul, Turkey.
2-Thiohydantoin derivatives, including different substitutions at N-1 and C-5 (5-methyl-, 5-isopropyl-, 1-acetyl-5-methyl-, and 1-acetyl-5-isopropyl-) (1-4, respectively), were synthesized by the known literature methods. In these synthetic pathways, it was reported that enantiomerically pure 2-thiohydantions were obtained in the absence of any solvent via the reaction of L-amino acids with thiourea (1&2) and via the reaction of L-amino acids with NHSCN and acetic anhydride (3&4). However, in this study, in contrary to the previous literature studies, racemic mixtures of 2-thiohydantoins were obtained although the same synthetic methods were used.
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