Volume No. 18
2022
Pages 1 - 1771
Table of Contents |
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| 124 | Full Research Paper |
| 17 | Review |
| 31 | Letter |
| 5 | Perspective |
| 1 | Commentary |
| 7 | Editorial |
- Letter
- Published 12 Sep 2022
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Scheme 1: a) Mechanochemical synthesis of g-PCN from sodium phosphide and trichlorotriazine (previous work [38]) ...
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Figure 1: PXRD patterns of g-h-PCN (green) and g-h-PCN300 (teal).
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Figure 2: XPS scans of a) C 1s, b) N 1s and c) P 2p for the pre-annealed g-h-PCN and d) C 1s, e) N 1s and f) ...
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Figure 3: 31P MAS NMR of a) g-h-PCN and b) g-h-PCN300. Asterisks denote spinning sidebands.
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Figure 4: Calculated structures for a) corrugated (edge facing), b) corrugated (single layer), c) layered g-h...
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- Published 13 Sep 2022
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Figure 1: Structures of 2-phosphaindolizine (1) and indolizine (2).
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Figure 2: Structures of 1-aza-2-phosphaindolizines 3, 3-aza-2-phosphaindolizines 4, and 1,3-diaza-2-phosphain...
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Figure 3: Transfer of the nitrogen lone-pair in 2-phosphaindolizines.
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Figure 4: Energy gap (ΔE) between HOMO of 1,3-butadiene and LUMO of 2-phosphaindolizine.
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Figure 5: Kohn–Shan HOMO of 1,3-butadiene and LUMOs of 2-phosphaindolizines computed at the B3LYP/6-31+G(d) l...
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- Perspective
- Published 14 Sep 2022
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Figure 1: Representation of (a) cavitation and elongational flow caused by pulsed ultrasonication, (b) mixer ...
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Scheme 1: (a) Mechanochemical activation of anthracene–endoperoxide mechanophore incorporated in the cross-li...
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Scheme 2: Mechanochemical activation of dendronized polymer-based compound 4 by ultrasonication and ball mill...
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Figure 2: Structure of cellulose and chitin and approximation to the structure of lignin.
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Figure 3: Tensile forces by ball milling change the conformation of a chitin model compound. This deformation...
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Figure 4: (a) Representation of a collision between the ball and a particle of a chitin sample and (b) mechan...
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Figure 5: (a) Ultrasound-induced ATRP using piezoelectric BaTiO3 and (b) mechanochemical atom transfer radica...
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Figure 6: Mechanochemical solid-state complexation of organic capsule 5 with fullerenes C70 in a planetary ba...
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Scheme 3: Comparative mechanochemical dissociation of the central C–C bond in TASN derivatives 6 and 8.
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- Review
- Published 15 Sep 2022
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Scheme 1: Structures of vicinal ketoesters and examples for their typical reactivity.
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Scheme 2: Doyle’s diastereoselective intramolecular aldol addition of α,β-diketoester.
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Scheme 3: Synthesis of euphorikanin A (16) by intramolecular, nucleophilic addition [6].
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Scheme 4: Ketoester cycloisomerization for the synthesis of preussochromone A (24) [10].
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Scheme 5: Diastereoselective, intramolecular aldol reaction of an α-ketoester 28 in the synthesis of (−)-preu...
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Scheme 6: Synthesis of an α-ketoester through Riley oxidation and its use in an α-ketol rearrangement in the ...
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Scheme 7: Azomethine imine cycloaddition towards the synthesis of the proposed structure of palau’amine (44) [19]....
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Scheme 8: Intramolecular diastereoselective carbonyl-ene reaction of an α-ketoester in the synthesis of jatro...
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Scheme 9: Grignard addition to an α-ketoester and subsequent Friedel–Crafts cyclization in the synthesis of (...
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Scheme 10: Diastereoselective addition to an auxiliary modified α-ketoester in the formal synthesis of (+)-cam...
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Scheme 11: Intramolecular photoreduction of an α-ketoester in the synthesis of (rac)-isoretronecanol (69) [26].
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Scheme 12: α-Ketoester as nucleophile in a Tsuji–Trost reaction in the synthesis of (rac)-corynoxine (76) [27].
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Scheme 13: Mannich reaction of an α-ketoester in the synthesis of (+)-gracilamine (83) [28].
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Scheme 14: Enantioselective aldol reaction using an α-ketoester in the synthesis of (−)-irofulven (87) [29].
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Scheme 15: Allylboration of a mesoxalic acid ester in the synthesis of (+)-awajanomycin (92) [30,31].
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Scheme 16: Condensation of a diamine with mesoxolate in the synthesis of (−)-aplaminal (96) [32].
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Scheme 17: Synthesis of mesoxalic ester amide 102 and its use in the synthesis of (rac)-cladoniamide G (103) [33].
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Scheme 18: The thermodynamically controlled, intramolecular aldol addition of a vic-tricarbonyl compound in th...
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- Full Research Paper
- Published 15 Sep 2022
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Scheme 1: Methods for the synthesis of thiazoles using active methylene ketones as starting materials.
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Scheme 2: Substrate scope. Reaction conditions: 1 (2 mmol), 2 (1 mmol), NH4I (0.1 mmol), ᴅʟ-alanine (1 mmol),...
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Scheme 3: Up-scaling experiment.
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Scheme 4: Control experiments.
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Scheme 5: The proposed mechanism for the one-pot electrochemical synthesis of 2-aminothiazoles mediated by NH4...
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- Full Research Paper
- Published 16 Sep 2022
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Scheme 1: C3–Si bond functionalization of biomass-derived 3-silylated furfural platforms.
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Scheme 2: Preparation of 3-silylated 2-furyl carbinols.
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Scheme 3: C–Si bond functionalization of 2,3-disubstituted furyl carbinols by 1,4-silyl migration.
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Scheme 4: Attempts of C3–Si bond functionalization promoted by intramolecular activation via alkoxide.
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Scheme 5: Alkoxide-promoted cyclic siloxane formation from 2-[(3-benzyldimethylsilyl)furyl] carbinol 4c.
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Scheme 6: TBAF-promoted cyclic siloxane formation from 2-[(3-benzyldimethylsilyl)furyl] carbinol 4c.
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Scheme 7: Pd-catalyzed arylation of 2-[(3-benzyldimethylsilyl)furyl] carbinol 4c.
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Scheme 8: Cu-catalyzed allylation and methylation of 2-[(3-benzyldimethylsilyl)furyl] carbinols. aCuI⋅PPh3 (1...
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- Full Research Paper
- Published 19 Sep 2022
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Scheme 1: Retrosynthetic scheme of the target molecule 1.
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Scheme 2: Synthesis of dihydrofuran-monoterpenoid 1. a) i. O3, −78 °C; ii. PPh3, rt, 76%; b) 1-bromobut-2-yne...
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Scheme 3: Racemic resolution of allenol 3 and synthesis of derivatives. a) Lipase AK, vinyl acetate, t-BuOMe,...
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- Full Research Paper
- Published 19 Sep 2022
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Scheme 1: Regioselective ferrocenoylation of the adenine anion 1 and its derivatives 2–6 substituted at the N6...
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Figure 1: 1H NMR spectrum (downfield region) of the reaction mixture (adenine anion 1 and FcCOCl) in DMF, tak...
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Figure 2: HOMO map of space distribution (left) of adenine anion (1) at the B3LYP/6-31+G(d) level of theory (...
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Figure 3: Dependence of N9-isomer product ratio (%), in the reaction between FcCOCl and adenine anions 1–6, o...
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Figure 4: B3LYP/6-31+G(d)/SDD optimized transition state structures for N7- (6-TSN7) and N9-ferrocenoylation (...
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Figure 5: Relation between the Gibbs free energy barrier (ΔG‡) for the N7-ferrocenoylation of C6-substituted ...
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- Full Research Paper
- Published 20 Sep 2022
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Figure 1: Polyphosphate, a ubiquitous phosphate storage molecule. Reported chain lengths range from three to ...
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Figure 2: Comparison of PPK1 and PPK2 enzymes. a) Reaction scheme; b) structure of the EcPPK1 monomer (PDB 1X...
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Figure 3: a) Kinases as ATP regeneration enzymes, exemplified by the hexokinase-catalysed ATP-dependent phosp...
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Figure 4: Time courses of reactions started with ADP catalysed by a) SmPPK2 and b) EcPPK1. Time courses of re...
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Figure 5: a) Ratio of product to substrate for the three nucleotide concentrations (0.5, 2, and 4 mM) used in...
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Figure 6: Time courses comparing EcPPK1 (blue) and SmPPK2 (green) for ATP synthesis (a) and ATP degradation (...
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- Review
- Published 21 Sep 2022
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Figure 1: Enzyme function of cytochrome P450 monooxygenases (CYPs). A) Typical net reaction of CYPs, resultin...
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Figure 2: Phylogenetic distribution of CYPs acting on triterpenoid and steroid scaffolds (red nodes) compared...
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Figure 3: CYPs modifying steroid (A), cucurbitacin steroid (B) and tetracyclic triterpene (C) backbones. Subs...
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Figure 4: CYPs modifying pentacyclic 6-6-6-6-6 triterpenes. Substructures in grey indicate regions where majo...
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Figure 5: CYPs modifying pentacyclic 6-6-6-6-5 triterpenes (A) and unusual triterpenes (B). Substructures in ...
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Figure 6: Recent examples of multifunctional CYPs in triterpenoid and steroid metabolism in plants that insta...
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- Full Research Paper
- Published 22 Sep 2022
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Figure 1: Chemical structures of (a) reported ionic TADF emitters for LEECs, (b) the MR-TADF emitter DiKTa an...
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Scheme 1: Synthesis of DiKTa-OBuIm and DiKTa-DPA-OBuIm.
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Figure 2: (a) HOMO and LUMO electron density distribution and orbital energies of DiKTa-OMe and DiKTa-DPA-OMe...
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Figure 3: (a) Cyclic and differential pulse voltammograms measured in degassed MeCN with 0.1 M [n-Bu4N]PF6 as...
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Figure 4: (a) Steady-state emission spectra of DiKTa-OBuIm and DiKTa-DPA-OBuIm in 1 wt % doped mCP films, λex...
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Figure 5: (a) Electroluminescence spectra of DiKTa-OBuIm (green curve), DiKTa-DPA-OBuIm (red curve) and 1% of ...
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- Full Research Paper
- Published 23 Sep 2022
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Figure 1: AIE-active molecule 1. (a) Structure of 1 with color-coded subunits AIE, lysine, and GCP. (b) Coars...
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Figure 2: 14-3-3ζ from (a) top and (b) side with the two monomers in red and blue. In the top view the centra...
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Figure 3: Workflow of the computational approach used in this study. The protein structure and the structure ...
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Figure 4: Log-scaled histogram of total energies at the final steps of all simulations. (a) Simulated anneali...
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Figure 5: Sampled positions of the AIE moiety colored according to the total energy of 1 from dark red (lowes...
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Figure 6: Minimum energy conformations of AIE ligand in the absence (a,b) and presence (c,d) of C-Raf peptide...
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- Letter
- Published 26 Sep 2022
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Scheme 1: a) Derivatives of primary amines in materials chemistry, pharmaceuticals, and agrochemicals; b) thi...
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Scheme 2: Substrate scope of borane-catalysed nitrile hydroboration with HBpin. Conditions: nitrile (0.50 mmo...
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Scheme 3: a) Proposed mechanism; b) H-B-9-BBN-catalysed heptanenitrile hydroboration (yield determined by 1H ...
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- Full Research Paper
- Published 27 Sep 2022
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Scheme 1: Synthesis of bis(chlorophenyl)acetylenes 3.
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Scheme 2: Synthesis of 1,2,3-tris(chlorophenyl)cyclopropenylium bromides 5 and tributyl(1,2,3-tris(chlorophen...
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Figure 1: ORTEP representations for cations 5c (a) and 6c (b) at the 50% probability level. Bromide anion and...
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Scheme 3: Synthesis of 3,4,5-tris(chlorophenyl)-1,2-diphosphacyclopentadienides 7 and 3,4,5-tris(chlorophenyl...
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Figure 2: Considered conformations of 8b-I and 8b-II.
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Figure 3: Top: experimental UV–vis spectra of 8с (black) and 8b (red). Bottom: broadened calculated UV–vis sp...
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Figure 4: Frontier orbitals of 8b-II contributing to absorption bands at about 380 nm.
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Figure 5: Cyclic voltammograms of 3,4,5-triaryl-1,2-diphosphaferrocenes 8b and 8c in CH3CN on glassy carbon e...
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- Perspective
- Published 29 Sep 2022
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Figure 1: Structure of halicin (1).
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Figure 2: Structures of compounds 2–7.
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Figure 3: Structures of compounds 8–12.
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Figure 4: Structures of compounds 13–17.
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Figure 5: Structures of compounds 18–21.
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Figure 6: Structures of compounds 22–36 and SAR of compound 22.
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Figure 7: Structures of compounds 37 and 38.
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Figure 8: Structures of compounds 39–44.
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Scheme 1: Retrosynthesis of pyrazolones A and B.
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Scheme 2: Reaction conditions: i: HF, SbF6, CCl4. ii: (CF3SO2)2Zn, t-BuO2H, CH2Cl2/H2O.
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Figure 9: Structures of compounds 49–61.
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Figure 10: Structures of compounds 62–65.
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Figure 11: Structures of compounds 66 and 67.
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- Letter
- Published 30 Sep 2022
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Figure 1: a) Proposed oxidative pathway for provision of GDP-ManA 5 from GDP-Man 1, C6 stereochemistry of 3 i...
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Scheme 1: Syntheses of C6-modified mannose 1-phosphates 13 and 17. Conditions a) PPh3, CBr4, DCM, rt, 75%; b)...
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Figure 2: Structure of 16 with ADPs rendered at the 50% probability level. Acetyl group disorder is omitted f...
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Scheme 2: Evaluation of enzymatic GDP-Man synthesis using C6-modified mannose 1-phosphates 13, 17, and 18; Y+...
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Figure 3: GMD function with probe 19 over 120 min (GMD (100 µg/mL), GDP sugars (50 µM), NAD+ (200 µM)). Dotte...
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- Published 04 Oct 2022
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Figure 1: Structures of leustroducsins and phoslactomycins.
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Figure 2: Synthetic strategy for the leustroducins and phoslactomycins.
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Figure 3: strategy for the synthesis of central fragment 4: nitroso Diels–Alder reaction.
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Scheme 1: A highly regio-and stereoselective nitroso Diels–Alder cycloaddition between Wightman’s reagent 6 a...
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Scheme 2: Hydrolysis of enol phosphate in the unprotected cycloadduct.
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Scheme 3: Attempts for hydrolysis of the enol phosphate under basic conditions.
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Scheme 4: Cleavage of enol phosphate with Red-Al.
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Scheme 5: Synthesis of the protected central fragment 11b.
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Scheme 6: Synthesis and derivatization of the lactone fragment.
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Scheme 7: Coupling reaction between alkyne 19 and ketone 11b.
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Scheme 8: Coupling reaction between vinyl iodide 20 and ketone 11b.
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Scheme 9: Oxidation of the acetal to the lactone.
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- Full Research Paper
- Published 05 Oct 2022
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Figure 1: The five distinct FC-type DTSs and the corresponding products.
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Figure 2: Bioinformatics analysis of the tad cluster. A) Phylogenetic tree of TadA and representative fungal ...
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Figure 3: HPLC–MS analysis of mycelial extracts from A. oryzae NSAR1 transformants. A) The HPLC profiles moni...
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Scheme 1: Biosynthesis of FC-type diterpenoids. A) The biosynthetic pathway of 1, 2 and 4. B) Cyclization mec...
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- Published 06 Oct 2022
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Scheme 1: Synthetic studies to obtain mono- and dipyrrole-substituted compounds.
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Scheme 2: The reaction of 5-phenyl-1,9-diformyldipyrromethane (1a) with pyrrole.
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Figure 1: 1H NMR spectrum of 2a in THF-d8.
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Figure 2: Electronic absorption spectrum of 2a in CHCl3.
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Scheme 3: [2 + 2] Mac Donald type condensation reaction.
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- Published 07 Oct 2022
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Figure 1: Structures of compounds 1–6.
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Figure 2: Key HMBC and 1H-1H COSY correlations of 1–3.
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Figure 3: (a) Key ROESY correlations of compound 1. (b) Experimental and calculated ECD spectra of 1.
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- Letter
- Published 10 Oct 2022
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Figure 1: Representative asymmetric Co–salen catalysts.
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Scheme 1: Synthetic approach to our unsymmetrical Co–salen catalyst 2f for the asymmetric synthesis of α-aryl...
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Scheme 2: Mechanochemical one-pot two-step synthesis of unsymmetrical salens 1a–h. Reaction conditions: salic...
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Scheme 3: Synthesis of unsymmetrical metal–salen complexes 2. Reaction conditions a: metal acetate hydrate (1...
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- Published 11 Oct 2022
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Figure 1: Adamantane-based tripodal scaffolds and current work.
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Scheme 1: A general strategy for the assembly of TAAD derivatives.
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Scheme 2: Synthesis of acyclic precursors to 3N-TAADs, 2N,1O-TAADs, and 1N,2O-TAADs.
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Scheme 3: Synthesis of 3N-TAADs, 2N,1O-TAADs, and 1N,2O-TAADs. *Yield based on compound 14.
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Scheme 4: Deprotection of TAAD 8b and subsequent complexation with phenylboronic acid.
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Scheme 5: Quaternization of TAADs 4c, 4e, 6a, and 8a followed by deprotection of N-Boc groups.
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Figure 2: General view of the 1,4,6,10-tetraazaadamantane motif in X-ray structures of the obtained N-TAAD de...
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Figure 3: (a) General structure of host–guest complexes of 3N-TAADs with water. (b) The general structure of ...
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Figure 4: (a) Dynamic processes in TAADs 4 and complexation with ROH. (b) Fragment of 1H NMR spectra of Bn-4c...
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- Editorial
- Published 12 Oct 2022
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Scheme 1: a) Mechanochemical PEG-400-assisted halogenation of phenols and anilines using NXS. b) Halogenation...
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Scheme 2: Mechanochemical palladium-catalyzed borylation protocol of aryl halides.
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Scheme 3: 1,2-Debromination of polycyclic imides, followed by in situ trapping of the dienophile by several d...
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Scheme 4: Synthesis of g-h-PCN from sodium phosphide and trichloroheptazine mediated by mechanochemistry.
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Scheme 5: Mechanochemical intra- and intermolecular C–N coupling reactions using DDQ as an oxidant.
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- Published 13 Oct 2022
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Figure 1: Levoglucosenone (1), known dimerization product 2, and adducts 3 and 4.
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Scheme 1: Proposed pathway for the formation of 5.
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Figure 2: 1H NMR spectra (500 MHz) of 1 (A), 1:1 1/PhCHO reaction mixture at 1 h at 60° C (B), mixture after ...
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Scheme 2: Known reactions giving 11, and reactions of dihydrolevoglucosenone 12 and aromatic aldehydes with D...
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- Letter
- Published 14 Oct 2022
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Figure 1: Structure of natural pyrophosphate and examples of NBPs (Z = Na or H).
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Figure 2: Structures of ATP analogues ApppI and ApppD (Z = Na or H).
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Scheme 1: Synthetic route to target compound ApppI(d2) (Z = TBA).
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- Published 17 Oct 2022
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Figure 1: Chiral phosphorus acids (CPAs) derived from BINOL, VAPOL, and SPINOL. R = H, Ph, 4-PhC6H4-, 4-β-nap...
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Scheme 1: The thiolic/thionic tautomeric equilibrium in thiophosphorus acids.
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Figure 2: Project strategy and requirements for C1-symmetrical CPAs.
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Figure 3: BINOL CPA and C1-symmetrical CPA targets 1–4.
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Scheme 2: Synthesis of tryptophol-derived thiophosphorus acid 1.
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Scheme 3: Synthesis of indole-derived thiophosphorus acid 2.
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Scheme 4: Synthesis of N-biphenyl-DOPO CPA 4.
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Scheme 5: Transfer hydrogenation of 2-phenylquinoline and transition-state proposed by Guinchard and coworker...
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- Published 18 Oct 2022
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Scheme 1: Utilization of Ph3BiCl2 for organic reactions involving desulfurization.
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Scheme 2: Synthesis of tafamidis (13).
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Scheme 3: Control experiments.
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Scheme 4: Proposed mechanism.
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- Published 20 Oct 2022
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Figure 1: Natural products YM-254890 and FR-900359.
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Figure 2: Diblock copolymers used for coating microelectrode arrays.
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Figure 3: An indirect method for detecting binding events.
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Scheme 1: A Cu(I)-catalyzed cross-coupling reaction on an array.
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Figure 4: A model study using an RGD peptide (C-PEG6-GGRGDGP) and integrin receptor (α5,β1).
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Figure 5: A failure in connection with the monitoring of binding events between a peptide and its G-protein t...
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Scheme 2: An array-based Chan–Lam coupling reaction.
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Figure 6: Potential for an immediate, rapid change in current. a) The binding event being monitored has alrea...
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Figure 7: Four cycles vs. twelve cycles and the effect on binding curve location.
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Figure 8: Repeating the experiment on different arrays. (a) A comparison between a 4-cycle placement reaction...
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Figure 9: Quantitative fluorescent study on variance of the polymer coating across the microelectrode surface...
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Scheme 3: A new method for decreasing the concentration of R6A on the surface of the electrodes.
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Figure 10: An initial study and the comparison of an R6A surface and a 1:1 R6A/cysteine methyl ester surface.
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Figure 11: Calibrating the array-based signaling experiment for monitoring small molecule G-protein interactio...
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Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite’s conformance
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- Published 25 Oct 2022
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Figure 1: ORTEP representation of triferrocenyl trithiophosphite showing 50% probability thermal ellipsoids.
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Figure 2: Optimized conformations and relative energies of four possible conformers of triferrocenyl trithiop...
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Figure 3: Calculated NBO charges on the Fe ions and hydrogen atoms for the optimized ttg conformer (left) and...
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Figure 4: Molecular structures in the solid state of a) (FcS)3P, b) (FcS)3PO [19], and c) (FcS)3PS [7] as establishe...
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Figure 5: Quantum chemically optimized conformations of the (PhS)3P molecule and their relative energies (kca...
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