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TETRAKIS(1-METHYLCYCLOPROPYL)ETHYLENE IN FOUR STEPS FROM alpha-METHYL-gamma-BUTYROLACTONE

A short and efficient synthesis of bis(1-methylcyclopropyl)ketone (6) via the spiro-acetal 4 from alpha-methyl-gamma-butyrolactone (1) has been found, and reductive dimerization of 6 by McMurry coupling yields tetrakis(1-methylcyclopropyl)ethylene (7) in competition with ring-opened products (8 and 9).

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Exploration of the interrupted Fischer indolization reaction

A convergent method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. The method is convergent, mild, operationally simple, broad in scope, and can be used to access enantioenriched products. In addition, our approach is amenable to the synthesis of furoindoline and pyrrolidinoindoline natural products as demonstrated by the concise formal total syntheses of physovenine and debromoflustramine B. The strategy will likely enable the synthesis of more complex targets such as the communesin alkaloids.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Identification of pheromone components and their binding affinity to the odorant binding protein CcapOBP83a-2 of the Mediterranean fruit fly, Ceratitis capitata

The Mediterranean fruit fly (or medfly), Ceratitis capitata (Wiedemann; Diptera: Tephritidae), is a serious pest of agriculture worldwide, displaying a very wide larval host range with more than 250 different species of fruit and vegetables. Olfaction plays a key role in the invasive potential of this species. Unfortunately, the pheromone communication system of the medfly is complex and still not well established. In this study, we report the isolation of chemicals emitted by sexually mature individuals during the “calling” period and the electrophysiological responses that these compounds elicit on the antennae of male and female flies. Fifteen compounds with electrophysiological activity were isolated and identified in male emissions by gas chromatography coupled to electroantennography (GC-EAG). Within the group of 15 identified compounds, 11 elicited a response in antennae of both sexes, whilst 4 elicited a response only in female antennae. The binding affinity of these compounds, plus 4 additional compounds known to be behaviourally active from other studies, was measured using C.capitata OBP, CcapOBP83a-2. This OBP has a high homology to Drosophila melanogaster OBPs OS-E and OS-F, which are associated with trichoid sensilla and co-expressed with the well-studied Drosophila pheromone binding protein LUSH. The results provide evidence of involvement of CcapOBP83a-2 in the medfly’s odorant perception and its wider specificity for (. E,. E)-alpha-farnesene, one of the five major compounds in medfly male pheromone emission. This represents the first step in the clarification of the C.capitata and pheromone reception pathway, and a starting point for further studies aimed towards the creation of new powerful attractants or repellents applicable in the actual control strategies.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Stereoselective Hydrogen Transfer Reactions Involving Acyclic Radicals. Tandem Substituted Tetrahydrofuran Formation and Stereoselective Reduction: Synthesis of the C17-C22 Subunit of Ionomycin

The tandem iodoetherification reaction and stereoselective reduction of acyclic redicals has been used in the stereocontrolled synthesis of substituted tetrahydrofurans.Such a tetrahydrofuran intermediate is regioselectively cleaved using Me2BBr to reveal the acyclic array 2 which represents the C17-C22 subunit of ionomycin.In experiments that provide for a better understanding of hydrogen transfer reactions involving acyclic radicals, a significant improvement in the stereoselectivity is observed when the two substituents at the stereogenic center alpha to the radicalare imbedded in a cycle (“cycle effect”).A mechanistic rationale is discussed.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Process for the preparation of alkyl 1-methylcyclopropanecarboxylate

Disclosed is a 4-step process for the preparation of alkyl esters of 1-methylcyclopropanecarboxylic acid which comprises the steps of (1) converting gamma-butyrolactone to alpha-methyl-gamma-butyrolactone; (2) converting the alpha-methyl-gamma-butyrolactone from step (1) to an alkyl 4-halo-2-methylbutyrate; (3) producing a xylene solution of the alkyl 4-halo-2-methylbutyrate; and (4) contacting the xylene solution of an alkyl 4-halo-2-methylbutyrate from step (3) with an alkali metal alkoxide under conditions of temperature and pressure which causes vaporization of (i) an alkanol as it is formed and (ii) an alkyl 1-methylcyclopropanecarboxylate as it is formed from the alkyl 4-halo-2-methylbutyrate. Also disclosed are processes whereby the alkyl 1-methylcyclopropanecarboxylate, prepared as described above, is converted to 1-methylcyclopropylamine.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Synthesis of Cannabinoid Model Compounds. Part 2): (3R,4R)-delta1(6)-Tetrahydrocannabinol-5″-oic Acid and 4″(R,S)-Methyl-(3R,4R)-delta1(6)-Tetrahydrocannabinol-5″-oic Acid

Two novel cannabinoid model compounds, (3R,4R)-Delta1(6)-tetrahydrocannabinol-5″-oic acid (22) and 4″(R,S)-methyl-(3R,4R)-Delta1(6)-tetrahydrocannabinol-5″-oic acid (23) were synthesized by acid-catalyzed condensation of (+)-trans-p-mentha-2,8-dien-1-ol (1) with the substituted resorcinols 18 and 19 obtained by a Wittig reaction between 3,5-bis(benzyloxy)benzaldehyde (7) and methyl 4-bromobutanoate (10) or methyl 4-bromo-2(R,S)-methylbutanoate (11) resp. with subsequent hydrogenation.The resulting methyl esters 20 and 21 were hydrolyzed to give acids 22 and 23.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Synthesis of butyrolactones by nickel-catalyzed reductive cyanation of alkynols in water

One-pot catalytic synthesis of butyrolactones from alkynols under mild conditions is described here. The methodology involves the use of the K 2[Ni(CN)4]/NaBH4 system in presence of KCN and water. According to the experimental evidences, a possible mechanism pathway is suggested, which involves the nickel-catalyzed reductive cyanation of alkynol, followed by nitrile hydration, reduction of double bond and lactonization.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Dienophilicity of imidazole in inverse electron demand Diels-Alder reactions; intramolecular reactions with 1,2,4-triazines

Imidazole and 2-phenylimidazole undergo intramolecular cycloadditions with 1,2,4-triazines tethered between an imidazole nitrogen and the triazinyl C3 position with a trimethylene chain to produce tetrahydro-1,5-naphthyridines following loss of N2 and a nitrile.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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N-Arylated pyrrolidin-2-ones and morpholin-3-ones as potassium channel openers.

Based on the most stable conformation of ZD6169, a series of N-arylated derivatives of oxazolidindione (2), morpholin-3-one (3-5), piperidin-2-one (6), and pyrrolidin-2-one (7-13) was synthesized and evaluated for potassium channel opening activity. In the in-vitro assays, N-(4-benzoylphenyl)-piperidin-2-on (6) and N-(4-benzoylphenyl)-3,3-dimethyl-pyrrolidin-2-one (9) demonstrated potent and selective relaxant activity at the bladder detrusor muscle [IC50, bladder)=7.4 and 6.7 microM, respectively; IC50 ratio (portal vein/bladder)=41 and 51, respectively].

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Iridium-catalyzed asymmetric hydrogenation of racemic alpha-substituted lactones to chiral diols

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic alpha-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (?)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem