Synthesis of the aggregation pheromone of Tribolium castaneum

• Biyu An,
• Xueyang Wang,
• Ao Jiao,
• Qinghua Bian and
• Jiangchun Zhong

Beilstein J. Org. Chem. 2025, 21, 510–514, doi:10.3762/bjoc.21.38

• with Grignard reagent, and oxidation with RuCl3/NaIO4. Keywords: aggregation pheromone; chiral 2-methyloxirane; red flour beetle; total synthesis; Introduction The red flour beetle, Tribolium castaneum Herbst (Coleoptera: Tenebrionidae), is a cosmopolitan, destructive stored product pest [1], which

• harmful to human health and this became a significant challenge to food security [6]. Long-term synthetic pesticide applications to control the red flour beetle has resulted in the development of resistance to organophosphates, pyrethroids, methyl carbamates, and neonicotinoids [7][8]. It became critical

• tosylate and a chiral Grignard reagent. The synthetic pheromone could be valuable for the control of the red flour beetle. The aggregation pheromone of Tribolium castaneum. Retrosynthetic analysis of the aggregation pheromone (4R,8R)-1. Synthesis of chiral tosylate (S)-10. Synthesis of chiral tosylate (R

Synthesis of disparlure and monachalure enantiomers from 2,3-butanediacetals

• Adam Drop,
• Hubert Wojtasek and
• Bożena Frąckowiak-Wojtasek

Beilstein J. Org. Chem. 2020, 16, 616–620, doi:10.3762/bjoc.16.57

• particularly interesting example, because it is also a component of the luring mixture used by the bolas spider Mastophora hutchinsoni [3][4]. (6R,7S,2E)-6,7-Epoxy-2-nonenal has been identified as a sex-aggregation pheromone of the red-necked longhorn beetle (Aromia bungii) [5] and its synthesis has been

Mechanistic investigations on multiproduct β-himachalene synthase from Cryptosporangium arvum

• Jan Rinkel and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2019, 15, 1008–1019, doi:10.3762/bjoc.15.99

• compound mixture need to be precise [1]. However, in some cases, compound mixtures have proven to be superior to the properties of the single compounds by evolution. Examples demonstrating this principle can be found in pheromone chemistry, like the bark beetle aggregation blend of ipsdienol, ipsenol and

18-Hydroxydolabella-3,7-diene synthase – a diterpene synthase from Chitinophaga pinensis

• Jeroen S. Dickschat,
• Jan Rinkel,
• Patrick Rabe,
• Arman Beyraghdar Kashkooli and
• Harro J. Bouwmeester

Beilstein J. Org. Chem. 2017, 13, 1770–1780, doi:10.3762/bjoc.13.171

• synthase from the beetle Phaedon cochleariae [33]. Similar small changes of the conditions, e.g., of the pH or the presence of different metal cofactors, may also change the product profile of a terpene synthase in different heterologous hosts. Changes in the product profile of terpene synthases depending

Identification, synthesis and mass spectrometry of a macrolide from the African reed frog Hyperolius cinnamomeoventris

• Markus Menke,
• Pardha Saradhi Peram,
• Iris Starnberger,
• Walter Hödl,
• Gregory F.M. Jongsma,
• David C. Blackburn,
• Mark-Oliver Rödel,
• Miguel Vences and
• Stefan Schulz

Beilstein J. Org. Chem. 2016, 12, 2731–2738, doi:10.3762/bjoc.12.269

• reported for (Z)-tetradec-5-en-13-olide (1) by Millar et al. [11], exhibiting a molecular ion at m/z 224. This macrolide, called cucujolide III, is used by the flat grain beetle Cryptolestes pusillus as pure (S)-enantiomer and by C. turcicus as a 33:67 R/S mixture [12], and acts as a synergist to the

• respective pheromones [11][13]. Microhydrogenation of the frog extract furnished 13-tetradecanolide, thus confirming compound A to be a 13-tetradecenolide. The double bond position in this macrolide likely is at C-5, because of the similarity of the mass spectrum to that of the beetle macrolide. Nevertheless

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• potent toxin that can ward of natural predators such as wolf spiders [48]. The initial isolation of pederin (3) included the collection and chemical analysis of 250,000 beetles. Later, the true producer was found to be an endosymbiotic Pseudomonas sp. within the female beetle which was identified by

• molecular analysis of the biosynthetic gene cluster of pederin (3) [49][50][51][52]. Beetle larvae hatching from pederin-containing eggs were less prone to predation by wolf spiders than pederin-free larvae, indicating the ecological significance of this secondary metabolite [53]. The biosynthetic gene

• beetle larvae, but also eventually causes the death of the tree. To propagate the fungus, adult beetles carry Entomocorticium sp. A in a specialized storage compartment called a mycangium from which the galleries within the inner bark of the host pine tree, housing the beetle larvae, are inoculated. The

Lateral ordering of PTCDA on the clean and the oxygen pre-covered Cu(100) surface investigated by scanning tunneling microscopy and low energy electron diffraction

• Stefan Gärtner,
• Benjamin Fiedler,
• Oliver Bauer,
• Antonela Marele and
• Moritz M. Sokolowski

Beilstein J. Org. Chem. 2014, 10, 2055–2064, doi:10.3762/bjoc.10.213

• ) from OCI Vacuum Microengineering. The LEED measurements were done at sample temperatures of 280–400 K using beam currents of 1–20 nA. The distortions of the LEED images due to the planar microchannel plate were corrected by a home-written software [10]. The second chamber contained a beetle-type

A protecting group-free synthesis of the Colorado potato beetle pheromone

• Zhongtao Wu,
• Manuel Jäger,
• Jeffrey Buter and
• Adriaan J. Minnaard

Beilstein J. Org. Chem. 2013, 9, 2374–2377, doi:10.3762/bjoc.9.273

• Zhongtao Wu Manuel Jager Jeffrey Buter Adriaan J. Minnaard Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands 10.3762/bjoc.9.273 Abstract A novel synthesis of the aggregation pheromone of the Colorado potato beetle, Leptinotarsa

• ; catalysis; Colorado potato beetle; Leptinotarsa decemlineata; oxidation; natural product; Introduction The Colorado potato beetle Leptinotarsa decemlineata, a worldwide pest causing considerable damage in the US annually, has developed resistance to more than 25 insecticides [1][2][3][4]. For crop

• insecticides controlling the Colorado potato beetle, and an attractive alternative is to use a pheromone management strategy. An important finding in this connection was the isolation of the male produced aggregation pheromone by Dickens and Oliver et al. in 2002 [7], which was subsequently identified as (S

On the proposed structures and stereocontrolled synthesis of the cephalosporolides

• Sami F. Tlais and
• Gregory B. Dudley

Beilstein J. Org. Chem. 2012, 8, 1287–1292, doi:10.3762/bjoc.8.146

• (Figure 1). Chalcogran, a sex pheromone secreted by the male bark beetle, is isolated from natural sources as a mixture of diastereomers. However, Byers et al showed that the spiroketal (2R,5R)-isomer induces the strongest responses from both females and males [16]. In such cases it is interesting to

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

• Robert Hilgraf,
• Nicole Zimmermann,
• Lutz Lehmann,
• Armin Tröger and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1256–1264, doi:10.3762/bjoc.8.141

• larvae of several leaf beetle species [49][50]. Subsequently, 30 may rearrange to the thermodynamically more stable, conjugated 21. Despite these results, there are still a lot of open questions concerning the biosynthesis of iridoids. Recently, it could be shown that leaf beetles may produce iridoid

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

• Nicole Zimmermann,
• Robert Hilgraf,
• Lutz Lehmann,
• Daniel Ibarra and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1246–1255, doi:10.3762/bjoc.8.140

• secretions of the abdominal defense glands of the rove beetle Creophilus maxillosus [39]. Interestingly, the structure of a' is relatively close to that of nepetalactone 7 and lactol 8, the sex pheromone of the grain aphid S. avenae [13] which keeps the second level in the investigated tetratrophic system

A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky

• Guolei Zhao,
• Chao Yang,
• Bing Li and
• Wujiong Xia

Beilstein J. Org. Chem. 2011, 7, 1342–1346, doi:10.3762/bjoc.7.158

• -phenethyloctadecanamide (1), was isolated from the beetle Ambrostoma quadriimpressum Motschulsky. The structure of the amide was determined by NMR and MS. The absolute configuration of compound 1 was confirmed by an asymmetric total synthesis, which was started from L-glutamic acid. The construction of the aliphatic

• chain was accomplished by the selective protection of the hydroxy groups and two-time implementation of the Wittig olefination reaction. Keywords: asymmetric synthesis; beetle; fatty acid amide; isolation; Introduction The leaf beetle Ambrostoma quadriimpressum Motschulsky (Coleoptera: Chrysomelidae

• with chemical defensive compounds. Insects are able to produce a vast array of biologically active secondary metabolites, which are used for defence purposes or as pheromones. In particular, the chemical defensive phenomenon of the beetle has been observed in Coleoptera [1][2]. Over the last few years

Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine

• Annabella F. Newton,
• Martin Rejzek,
• Marie-Lyne Alcaraz and
• Robert A. Stockman

Beilstein J. Org. Chem. 2008, 4, No. 4, doi:10.1186/1860-5397-4-4

• isolated from a ladybird beetle Hippodamia convergens by Tursch and co-workers in 1972 [3]. The structure of hippodamine (1) was established two years later by the same group [4] on the basis of a single-crystal X-ray diffraction experiment (Figure 1). Epi-hippodamine (2) is its unnatural isomer with an