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Female-Produced Sex Pheromone of Tetrastichus planipennisi, a Parasitoid Introduced for Biological Control of the Invasive Emerald Ash Borer, Agrilus planipennis

The Asian eulophid wasp Tetrastichus planipennisi is being released in North America as a biocontrol agent for the emerald ash borer (Agrilus planipennis), a very destructive invasive buprestid beetle that is devastating ash trees (Fraxinus spp.). We identified, synthesized, and tested a female-produced sex pheromone for the wasp. The key component eliciting behavioral responses from male wasps in flight tunnel bioassays was identified as (6S,10S)-(2E,4E,8E)-4,6,8,10-tetramethyltrideca-2,4,8-triene. Female specificity was demonstrated by gas chromatographic (GC) comparison of male and female volatile emissions and whole body extracts. The identification was aided by coupled gas chromatography/mass spectrometry analysis, microchemical reactions, NMR, GC analyses with a chiral stationary phase column, and matching GC retention times and mass spectra with those of synthetic standards. The tetramethyl-triene hydrocarbon was synthesized as a mixture of two enantiomeric pairs of diastereomers, and as the pure insect-produced stereoisomer. In flight-tunnel bioassays, males responded to both the natural pheromone and the chiral synthetic material by upwind flight and landing on the source. In contrast, the mixture of four stereoisomers was not attractive, indicating that one or more of the ?unnatural? stereoisomers antagonized attraction. Field trials, using yellow pan traps baited with natural pheromone, captured significantly more male wasps than control traps over a four week trial. The identified pheromone could increase the efficiency and specificity of the current detection methods for Tetrastichus planipennisi and aid in the determination of parasitoid establishment at release sites.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H453NO – PubChem

 

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ALKENYLDIARYLMETHANES, FUSED ANALOGS AND SYNTHESES THEREOF

Non-nucleoside inhibitors of HIV-1 reverse transcriptase are described. Such inhibitors may be used as part of a combination therapy to treat HIV infection. Compounds described herein exhibit antiviral potency. In addition, compounds described herein exhibit metabolic stability. Also described herein are processes for preparing Non-nucleoside inhibitors of HIV-1 reverse transcriptase

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Oxazolidine – Wikipedia,
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Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

The review highlights the hydantoin syntheses presented from the point of view of the preparation methods. Novel synthetic routes to various hydantoin structures, the advances brought to the classical methods in the aim of producing more sustainable and environmentally friendly procedures for the preparation of these biomolecules, and a critical comparison of the different synthetic approaches developed in the last twelve years are also described. The review is composed of 95 schemes, 8 figures and 528 references for the last 12 years and includes the description of the hydantoin-based marketed drugs and clinical candidates.

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Oxazolidine – Wikipedia,
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A modular and organocatalytic approach to gamma-butyrolactone autoregulators from Streptomycetes

A general synthesis of optically active gamma-butyrolactone autoregulators is developed by a two-step sequence to assemble 2,3-trans-disubstituted butyrolactones in high yields and enantioselectivities; the scope of this reaction was elaborated by setting up a library of alkyl-substituted butyrolactones and the synthesis of the autoregulators IM-2 and VB-D. The Royal Society of Chemistry.

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Nucleophilic reactivities of imide and amide anions

(Figure presented) The kinetics of the reactions of amide and imide anions 2a-o with benzhydrylium ions 1a-i and structurally related quinone methides 1j-q have been studied by UV-vis spectroscopy in DMSO and acetonitrile solution. The second-order rate constants (log k2) correlated linearly with the electrophilicity parameters E of 1a-q according to the correlation log k 2 = s(N + E) (Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957), allowing us to determine the nucleophilicity parameters N and the nucleophile-specific parameters s for these nucleophiles. The reactivities of all sulfonamide and diacylimide anions are found in a relatively small range (15 < N < 22). Comparison with structurally related carbanions revealed that amide and imide anions are less reactive than carbanions of the same pK aH. These effects can be attributed to the absence of resonance stabilization of one of the lone pairs in the amide or imide anions. As amide and imide anions are exclusively attacked at nitrogen by benzhydrylium ions, Kornblums interpretation of the ambident reactivity of amide anions has to be revised. Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Reference of 497-25-6. In my other articles, you can also check out more blogs about 497-25-6

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Oxazolidine – Wikipedia,
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NHC-Catalyzed intramolecular redox amidation for the synthesis of functionalized lactams

A very efficient NHC-catalyzed lactamization reaction is reported. For most cases, the ring expansion reaction proceeds to cleanly furnish five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. Evidence is presented suggesting a dual role for the stoichiometric base: (1) deprotonation of the triazolium precatalyst and (2) activation of the nitrogen leaving group through hydrogen bonding.

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Oxazolidine – Wikipedia,
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Challenges and approaches in the discovery of human immunodeficiency virus type-1 non-nucleoside reverse transcriptase inhibitors

The type I human immunodeficiency virus (HIV-1) pandemic affecting over 37 million people worldwide continues, with 1.8 million people newly infected each year. Highly active antiretroviral therapy is efficient at reducing viral load and nearly one-half of the infected population is on treatment. One of the most successful approaches for the treatment of HIV infections is the use of inhibitors for human immunodeficiency virus type-1 reverse transcriptase (HIV-1 RT). At present, there are six nonnucleoside reverse transcriptase inhibitors (NNRTIs) approved for clinical use: nevirapine (NVP), delavirdine (DLV), efavirenz (EFV), etravirine (ETV), rilpivirine (RPV), and elsulfavirine. In this review, we will cover the development of different classes of NNRTIs over the last two decades. We will give an overview of traditional medicinal chemistry strategies for structural modification as bioisosterism principles, scaffold hopping, substitute decoration, and molecular hybridization. Furthermore, computer-aid design as virtual screening, de novo design and free-energy perturbation will be described in details.

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Highly regio- and stereocontrolled synthesis of beta-substituted alpha-tributylstannyl enamides

The regio- and stereocontrolled synthesis of beta-substituted alpha-stannyl enamides is reported starting from internal ynamides. The synthesis of new ynamides as well as bis-ynamides is also described. Finally first examples of successful cross-coupling to afford alpha/beta-disubstituted enamides are also reported.

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HETEROCYCLIC COMPOUND

The present invention provides a compound having a superior JAK inhibitory action, which is useful as an agent for the prophylaxis or treatment of autoimmune diseases (rheumatoid arthritis, psoriasis, inflammatory bowel disease, Sjogren’s syndrome, Behcet’s disease, multiple sclerosis, systemic lupus erythematosus, etc.), cancer (leukemia, uterine leiomyosarcoma, prostate cancer, multiple myeloma, cachexia, myelofibrosis, etc.) and the like, or a salt thereof. The present invention relates to a compound represented by the formula wherein each symbol is as defined in the specification, or a salt thereof.

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Copper-catalyzed coupling of amides and carbamates with vinyl halides

(Matrix presented) A general and efficient copper-catalyzed method for the amidation of vinyl bromides and iodides has been developed. This protocol uses a combination of 5 mol % copper iodide and 20 mol % N,N?-dimethyl ethylenediamine. Substrates bearing ester, silyl ether, and amino groups were successfully coupled under the reaction conditions. The double bond geometry of the vinyl halides was retained under the reaction conditions.

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