Beilstein Journal of Organic Chemistry This is an RSS file. You can use it to subscribe to this data in your favourite RSS reader or to display this data on your own website or blog.

Transition-metal-catalyzed C – H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview
Abstract The last decade has witnessed the emergence of innovative synthetic tools for the synthesis of fluorinated molecules. Among these approaches, the transition-metal-catalyzed functionalization of various scaffolds with a panel of fluorinated groups (XRF, X = S, Se, O) offered straightforward access to high value-added compounds. This review will highlight the main advances made in the field with the transition-metal-catalyzed functionalization of C(sp2) and C(sp3) centers with SCF3, SeCF3, or OCH2CF3 groups among others, by C–H bond activation. The scope and limitations of these transformations are discussed i...
Source: Beilstein Journal of Organic Chemistry - April 17, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: C – H bond activation emergent fluorinated groups homogeneous catalysis organofluorine chemistry palladium synthetic method Review Source Type: research

Mechanochemical solid state synthesis of copper(I)/NHC complexes with K3PO4
Abstract A protocol for the mechanochemical synthesis of copper(I)/N-heterocyclic carbene complexes using cheap and readily available K3PO4 as base has been developed. This method employing a ball mill is amenable to typical simple copper(I)/NHC complexes but also to a sophisticated copper(I)/N-heterocyclic carbene complex bearing a guanidine moiety. In this way, the present approach circumvents commonly employed silver(I) complexes which are associated with significant and undesired waste formation and the excessive use of solvents. The resulting bifunctional catalyst has been shown to be active in a variety of reduction/...
Source: Beilstein Journal of Organic Chemistry - April 14, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: ball mill bifunctional catalysis catalytic hydrogenations copper mechanochemical synthesis N-heterocyclic carbenes Letter Source Type: research

Dipeptide analogues of fluorinated aminophosphonic acid sodium salts as moderate competitive inhibitors of cathepsin C
Abstract In this paper, we present the solvolysis reaction of dipeptide analogues of fluorinated aminophosphonates with simultaneous quantitative deprotection of the amino group. To the best of our knowledge, this work is the first reported example of the application of fluorinated aminophosphonates in cathepsin C inhibition studies. The new molecules show moderate inhibition of the cathepsin C enzyme, which opens the door to consider them as potential therapeutic agents. Overall, our findings provide a new avenue for the development of fluorinated aminophosphonate-based inhibitors. Beilstein J. Org. Chem. 2023, 19, 434&#...
Source: Beilstein Journal of Organic Chemistry - April 12, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: aminophosphonates cathepsin C dipeptide fluorine solvolysis Full Research Paper Source Type: research

Asymmetric synthesis of a stereopentade fragment toward latrunculins
Abstract Latrunculins are marine toxins used in cell biology to block actin polymerization. The development of new synthetic strategies and methods for their synthesis is thus important in order to improve, modulate or control this biological value. The total syntheses found in the literature all target similar disconnections, especially an aldol strategy involving a recurrent 4-acetyl-1,3-thiazolidin-2-one ketone partner. Herein, we describe an alternative disconnection and subsequent stereoselective transformations to construct a stereopentade amenable to latrunculin and analogue synthesis, starting from (+)-β-citro...
Source: Beilstein Journal of Organic Chemistry - April 3, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: allylation aldol reaction latrunculins stereocontrol total synthesis Letter Source Type: research

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities
Abstract The combretastatin D series and its analogues, corniculatolides and isocorniculatolides belong to a class of macrocycles called cyclic diaryl ether heptanoids (DAEH). This review is intended to highlight the structure elucidation, biosynthesis, and biological activity of these compounds as well as the use of different strategies for their synthesis. Beilstein J. Org. Chem. 2023, 19, 399–427. doi:10.3762/bjoc.19.31 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - March 29, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: combretastatin D corniculatolide isocorniculatolide macrocycles Review Source Type: research

Discrimination of β -cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis
Abstract The goal of the study was the discrimination of β-cyclodextrin (β-CD)/hazelnut (Corylus avellana L.) oil/antioxidant ternary complexes through Fourier-transform infrared spectroscopy coupled with principal component analysis (FTIR–PCA). These innovative complexes combine the characteristics of the three components and improve the properties of the resulting material such as the onsite protection against oxidative degradation of hazelnut oil unsaturated fatty acid glycerides. Also, the apparent water solubility and bioaccessibility of the hazelnut oil components and antioxidants can be increased, as...
Source: Beilstein Journal of Organic Chemistry - March 28, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: antioxidant cyclodextrin flavonoid hazelnut vegetable oil ternary supramolecular inclusion complex Full Research Paper Source Type: research

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview
Abstract Among all the available approaches in organic synthesis, the “click chemistry” protocol is very common nowadays to covalently connect two diverse moieties in a single framework. Therefore, this review focuses on the synthesis and photophysical studies of β- and meso-substituted and 1,2,3-triazole-fused porphyrin conjugates. All of the porphyrin conjugates discussed here are synthesized via a copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction between an azide and a terminal alkyne, also popular as "click reaction" or CuAAC reaction. Moreover, the 1,2,3-triazole ring also serve...
Source: Beilstein Journal of Organic Chemistry - March 22, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: azide – alkyne click chemistry CuAAC 1,3-dipolar cycloaddition porphyrin 1,2,3-triazole Review Source Type: research

Group 13 exchange and transborylation in catalysis
Abstract Catalysis is dominated by the use of rare and potentially toxic transition metals. The main group offers a potentially sustainable alternative for catalysis, due to the generally higher abundance and lower toxicity of these elements. Group 13 elements have a rich catalogue of stoichiometric addition reactions to unsaturated bonds but cannot undergo the redox chemistry which underpins transition-metal catalysis. Group 13 exchange reactions transfer one or more groups from one group 13 element to another, through σ-bond metathesis; where boron is both of the group 13 elements, this is termed transborylation. Th...
Source: Beilstein Journal of Organic Chemistry - March 21, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: catalysis group 13 exchange hydroboration main group transborylation Review Source Type: research

Synthesis and reactivity of azole-based iodazinium salts
Abstract A systematic investigation of imidazo- and pyrazoloiodazinium salts is presented. Besides a robust synthetic protocol that allowed us to synthesize these novel cyclic iodonium salts in their mono- and dicationic forms, we gained in-depth structural information through single-crystal analysis and demonstrated the ring opening of the heterocycle-bridged iodonium species. For an exclusive set of dicationic imidazoiodaziniums, we show highly delicate post-oxidation functionalizations retaining the hypervalent iodine center. Beilstein J. Org. Chem. 2023, 19, 317–324. doi:10.3762/bjoc.19.27 (Source: Beilstei...
Source: Beilstein Journal of Organic Chemistry - March 16, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: building block heterocycles hypervalent compounds iodonium salts one-pot synthesis Full Research Paper Source Type: research

Recommendations for performing measurements of apparent equilibrium constants of enzyme-catalyzed reactions and for reporting the results of these measurements
Abstract The measurement of values of apparent equilibrium constants K′ for enzyme-catalyzed reactions involve a substantial number of critical details, neglect of which could lead to systematic errors. Here, interferences, impurities in the substances used, and failure to achieve equilibrium are matters of substantial consequence. Careful reporting of results is of great importance if the results are to have archival value. Thus, attention must be paid to the identification of the substances, specification of the reaction(s), the conditions of reaction, the definition of the equilibrium constant(s) and standard stat...
Source: Beilstein Journal of Organic Chemistry - March 15, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: enzyme-catalyzed reactions equilibrium constant standards thermodynamics Perspective Source Type: research

Continuous flow synthesis of 6-monoamino-6-monodeoxy- β -cyclodextrin
Abstract The first continuous flow method was developed for the synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin starting from native β-cyclodextrin through three reaction steps, such as monotosylation, azidation and reduction. All reaction steps were studied separately and optimized under continuous flow conditions. After the optimization, the reaction steps were coupled in a semi-continuous flow system, since a solvent exchange had to be performed after the tosylation. However, the azidation and the reduction steps were compatible to be coupled in one flow system obtaining 6-monoamino-6-monodeoxy-β-cycl...
Source: Beilstein Journal of Organic Chemistry - March 9, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: azidation continuous flow β -cyclodextrin H-cube 6-monoamino-6-monodeoxy- monosubstitution reduction Full Research Paper Source Type: research

Synthesis, α -mannosidase inhibition studies and molecular modeling of 1,4-imino- ᴅ -lyxitols and their C-5-altered N-arylalkyl derivatives
Abstract A synthesis of 1,4-imino-ᴅ-lyxitols and their N-arylalkyl derivatives altered at C-5 is reported. Their inhibitory activity and selectivity toward four GH38 α-mannosidases (two Golgi types: GMIIb from Drosophila melanogaster and AMAN-2 from Caenorhabditis elegans, and two lysosomal types: LManII from Drosophila melanogaster and JBMan from Canavalia ensiformis) were investigated. 6-Deoxy-DIM was found to be the most potent inhibitor of AMAN-2 (Ki = 0.19 μM), whose amino acid sequence and 3D structure of the active site are almost identical to the human α-mannosidase II (GMII). Although 6-deoxy-...
Source: Beilstein Journal of Organic Chemistry - March 6, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: glycosidase inhibitor Golgi mannosidase II iminosugar inhibition molecular modeling Full Research Paper Source Type: research

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series
Abstract Terpene compounds probably represent the most diversified class of secondary metabolites. Some classes of terpenes, mainly diterpenes (C20) and sesterterpenes (C25) and to a lesser extent sesquiterpenes (C15), share a common bicyclo[3.6.0]undecane core which is characterized by the presence of a cyclooctane ring fused to a cyclopentane ring, i.e., a [5-8] bicyclic ring system. This review focuses on the different strategies elaborated to construct this [5-8] bicyclic ring system and their application in the total synthesis of terpenes over the last two decades. The overall approaches involve the construction of th...
Source: Beilstein Journal of Organic Chemistry - March 3, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: 5-8 bicycle cyclization strategies terpenes Review Source Type: research

An efficient metal-free and catalyst-free C – S/C – O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides
Abstract An operationally simple and metal-free approach is described for the synthesis of pyrazole-tethered thioamide and amide conjugates. The thioamides were generated by employing a three-component reaction of diverse pyrazole C-3/4/5 carbaldehydes, secondary amines, and elemental sulfur in a single synthetic operation. The advantages of this developed protocol refer to the broad substrate scope, metal-free and easy to perform reaction conditions. Moreover, the pyrazole C-3/5-linked amide conjugates were also synthesized via an oxidative amination of pyrazole carbaldehydes and 2-aminopyridines using hydrogen peroxide a...
Source: Beilstein Journal of Organic Chemistry - March 2, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: C – S/O bond formation metal-free oxidative amidation pyrazole carbaldehydes sulfur insertion thioamides Full Research Paper Source Type: research

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “ green ” solvent dihydrolevoglucosenone
In this study, we investigated the cationic ring-opening polymerization of 2-ethyl-2-oxazoline and 2-butyl-2-oxazoline using a variety of initiators in the recently commercialized "green" solvent dihydrolevoglucosenone (DLG). Detailed 1H NMR spectroscopic analysis was performed to understand the influence of the temperature and concentration on the polymerization process. Size exclusion chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry were performed to determine the molar mass of the resulting polymers. Our work shows clearly that the solvent is not inert under the c...
Source: Beilstein Journal of Organic Chemistry - February 28, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: 2-alkyl-2-oxazolines matrix-assisted laser desorption/ionization mass spectrometry nuclear magnetic resonance polymerization kinetics Full Research Paper Source Type: research