On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

Eirinaios I. Vrettos,
Gábor Mező and
Andreas G. Tzakos

Review
Published 26 Apr 2018

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1. Graphical Abstract
2. Figure 1: Conventional chemotherapy versus targeted chemotherapy. Black color = Solid malignant tumor; red = ...
  
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3. Figure 2: A. General structural architecture of the ideal navigated drug delivery system [31]. B. General structu...
  
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4. Figure 3: Binding and penetration mechanism of iRGD. The iRGD peptide is accumulated on the surface of αv int...
  
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5. Figure 4: Representative examples of anticancer drugs utilized for the construction of PDCs. The most usual c...
  
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6. Figure 5: Illustration of the drug release mechanism from the self-immolative spacer PABC conjugated to a tum...
  
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7. Figure 6: Structures of the PDCs named AN-152 and AN-207.
  
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8. Figure 7: Structure of the PDC named AN-238.
  
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9. Figure 8: Chemical structure and synthetic scheme for the PDC ANG1005. (A) ANG1005 is composed of three molec...
  
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10. Figure 9: Structure of oxime linked Dau–GnRH-III conjugate with or without cathepsin B labile spacer and thei...
  
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11. Figure 10: Synthesis of the most effective GnRH-III–Dau conjugate with two drug molecules [153].
  
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12. Figure 11: Structures of the four different PDCs of D-Lys⁶-GnRH-I and gemcitabine (GSG, GSG₂, 3G, 3G₂) [19].
  
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13. Figure 12: Structures of (A) native sunitinib; (B) SAN1 analog of sunitinib and (C) assembled PDC named SAN1GS...
  
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14. Figure 13: Synthetic scheme for the formation of GSG and the unexpected side product [156].
  
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15. Figure 14: Illustration of uncharted guanidinium peptide coupling reagent side reactions during PDCs synthesis ...
  
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16. Figure 15: Putative mechanism for the formation of the uronium side product [156].
  
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Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

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Local energy decomposition analysis of hydrogen-bonded dimers within a domain-based pair natural orbital coupled cluster study

Ahmet Altun,
Frank Neese and
Giovanni Bistoni

Full Research Paper
Published 25 Apr 2018

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1. Graphical Abstract
2. Figure 1: The conformers of (a) water dimer and (b) HF dimer.
  
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3. Figure 2: Schematic representation of strong pair excitations in the framework of the DLPNO-CCSD(T) method. E...
  
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4. Figure 3: Dissociation curve of Conf1 of water dimer as a function of the H-bond distance. Its nearly linear ...
  
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5. Figure 4: Decomposed HF energy terms (top), and correlation energy terms (bottom) of Conf1 of water dimer as ...
  
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6. Figure 5: Comparison of total interaction, electrostatic interaction, and London dispersion energies calculat...
  
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Beilstein J. Org. Chem. 2018, 14, 919–929, doi:10.3762/bjoc.14.79

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Development of novel cyclic NGR peptide–daunomycin conjugates with dual targeting property

Andrea Angelo Pierluigi Tripodi,
Szilárd Tóth,
Kata Nóra Enyedi,
Gitta Schlosser,
Gergely Szakács and
Gábor Mező

Full Research Paper
Published 25 Apr 2018

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1. Graphical Abstract
2. Figure 1: Schematic synthesis of cyclic KNGRE (A) and XNGRE (B) drug conjugates. a) Mtt-cleavage: 2% TFA/DCM;...
  
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3. Figure 2: (A) HT1080 and (B) HT-29 cells. Uptake of conjugate 1 (light green); 2 (red); 3 (light blue); 4 (pi...
  
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Beilstein J. Org. Chem. 2018, 14, 911–918, doi:10.3762/bjoc.14.78

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Volatiles from three genome sequenced fungi from the genus Aspergillus

Jeroen S. Dickschat,
Ersin Celik and
Nelson L. Brock

Full Research Paper
Published 24 Apr 2018

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1. Graphical Abstract
2. Figure 1: Total ion chromatograms of headspace extracts from A) Aspergillus fischeri NRRL 181, B) Aspergillus...
  
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3. Scheme 1: Volatiles from Aspergillus fischeri. For all chiral compounds in Schemes 1–5 the relative configura...
  
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4. Scheme 2: Biosynthesis of bisabolanes and related terpenes in A. fischeri.
  
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5. Scheme 3: Biosynthesis of daucanes in A. fischeri.
  
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6. Scheme 4: Volatiles from A. kawachii. A) Proposed biosynthesis of sesquiterpenes, B) other identified volatil...
  
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7. Scheme 5: Volatiles from A. clavatus.
  
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Beilstein J. Org. Chem. 2018, 14, 900–910, doi:10.3762/bjoc.14.77

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Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

Fabiana Pandolfi,
Isabella Chiarotto and
Marta Feroci

Full Research Paper
Published 23 Apr 2018

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1. Graphical Abstract
2. Scheme 1: The Corey–Fuchs reaction.
  
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3. Scheme 2: Electrochemical reduction of a carbon–halogen bond.
  
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4. Scheme 3: Electrochemical synthesis of vinyl bromides [25].
  
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5. Scheme 4: Scope of this work.
  
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6. Figure 1: Voltammetric curves of 1a 0.020 mol dm⁻³; Pt, glassy carbon (GC) or Ag cathode. ν = 0.2 V s⁻¹, T = ...
  
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7. Scheme 5: Possible products from the electrolysis of 2-(2,2-dibromovinyl)naphthalene (1a).
  
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8. Figure 2: Variation of the amounts of 1a, 2a, and 3a with the number of Faradays of 1a.
  
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9. Scheme 6: Mechanistic hypothesis for the synthesis of alkyne 2a and bromoalkyne 3a from 2-(2,2-dibromovinyl)n...
  
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10. Scheme 7: Possible reaction using NaClO₄ as supporting electrolyte.
  
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11. Scheme 8: Electrochemical synthesis of 9-ethyl-3-ethynyl-9H-carbazole (2b).
  
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12. Scheme 9: Electrochemical synthesis of 1-ethynyl-4-methoxybenzene (2c).
  
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Beilstein J. Org. Chem. 2018, 14, 891–899, doi:10.3762/bjoc.14.76

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An efficient and facile access to highly functionalized pyrrole derivatives

Meng Gao,
Wenting Zhao,
Hongyi Zhao,
Ziyun Lin,
Dongfeng Zhang and
Haihong Huang

Full Research Paper
Published 20 Apr 2018

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1. Graphical Abstract
2. Figure 1: Representative pyrrolo[3,4-c]pyrrole-1,3-diones and polysubstituted pyrrole derivatives.
  
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3. Scheme 1: Synthetic pathway for the preparation of pyrrolo[3,4-c]pyrrole-1,3-diones and highly substituted py...
  
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4. Scheme 2: Scope of one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones 12a–k. General reaction conditions: ...
  
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5. Scheme 3: Scope of the synthesis of highly substituted pyrrole derivatives 13a–n. General reaction conditions...
  
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6. Scheme 4: Synthesis of 13k from 12d and ethylamine.
  
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Beilstein J. Org. Chem. 2018, 14, 884–890, doi:10.3762/bjoc.14.75

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Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence

Amarendar Reddy Maddirala and
Peter R. Andreana

Full Research Paper
Published 18 Apr 2018

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1. Graphical Abstract
2. Scheme 1: Previously reported post-Ugi-4CR methods for the synthesis of 2-oxindoles and spirocyclic 2-oxindol...
  
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3. Scheme 2: Post-Ugi-4CR/transamidation/cyclization sequence.
  
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4. Scheme 3: Base-promoted intramolecular 5-endo-dig cyclization.
  
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5. Figure 1: ORTEP diagram of compound 7a.
  
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6. Figure 2: Readily and synthetically accessible starting materials.
  
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7. Scheme 4: Reaction scope with varying combinations of substrates.
  
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8. Scheme 5: Synthesis of 5-chloro-1'-phenylspiro[indoline-3,2'-pyrrolidine]-2,5'-dione (8a).
  
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9. Figure 3: Small molecule library of spiro[indoline-3,2'-pyrrolidine]-2,5'-dione analogs.
  
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10. Scheme 6: Method applicability for the one-pot synthesis of 5-HT6 receptor antagonist 8j [53].
  
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Beilstein J. Org. Chem. 2018, 14, 875–883, doi:10.3762/bjoc.14.74

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Two novel blue phosphorescent host materials containing phenothiazine-5,5-dioxide structure derivatives

Feng-Ming Xie,
Qingdong Ou,
Qiang Zhang,
Jiang-Kun Zhang,
Guo-Liang Dai,
Xin Zhao and
Huai-Xin Wei

Full Research Paper
Published 17 Apr 2018

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1. Graphical Abstract
2. Scheme 1: Synthetic routes of CEPDO and CBPDO.
  
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3. Figure 1: Structures and molecular orbitals of (a) CEPDO and (b) CBPDO.
  
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4. Figure 2: UV–vis absorption and photoluminescence spectra in DCM solution (1 × 10⁻⁵ M and 1 × 10⁻⁶ M, respect...
  
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5. Figure 3: Cyclic voltammograms for CEPDO and CBPDO in DCM solution.
  
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6. Figure 4: DSC and TGA curves of CEPDO and CBPDO.
  
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Beilstein J. Org. Chem. 2018, 14, 869–874, doi:10.3762/bjoc.14.73

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Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis

Tatiana Golub and
James Y. Becker

Full Research Paper
Published 16 Apr 2018

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1. Graphical Abstract
2. Scheme 1: Anodic oxidation of amides.
  
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3. Scheme 2: Anodic oxidation of an amide in the presence of alkene.
  
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4. Scheme 3: Intramolecular cyclization via anodic oxidation of an eneamide.
  
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5. Scheme 4: Anodic bond cleavages in amides of type Ph₂CHCONHAr.
  
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6. Scheme 5: Type of products obtained (n = 0, 1, 2).
  
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7. Scheme 6: Synthesized cyclic N-acyl and N-sulfonyl piperidines for electrolysis.
  
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8. Scheme 7: Type of bisamides (derived from diamines) studied (n = 2, 3, 4).
  
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9. Scheme 8: Type of products obtained from anodic oxidation of II-3.
  
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10. Scheme 9: Anodic splitting of C–C bond in bisamides in the presence of LiClO₄ electrolyte.
  
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11. Scheme 10: Anodic splitting of C–C bond in bisamides in the presence of Et₄NBF₄ electrolyte.
  
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12. Scheme 11: A suggested mechanism for anodic methoxylation of amides.
  
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13. Scheme 12: Mechanisms of formation of fragmentation products.
  
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Beilstein J. Org. Chem. 2018, 14, 861–868, doi:10.3762/bjoc.14.72

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A stereoselective and flexible synthesis to access both enantiomers of N-acetylgalactosamine and peracetylated N-acetylidosamine

Bettina Riedl and
Walther Schmid

Letter
Published 13 Apr 2018

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1. Graphical Abstract
2. Figure 1: Four possible isomers reachable through the presented approach.
  
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3. Scheme 1: Sharpless epoxidation to gain D-galacto- 5a and L-galacto-configured epoxythreitol 5b.
  
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4. Scheme 2: Reagents and conditions: a) i) (COCl)₂, DMSO, Et₃N, DCM, ii) triethyl phosphonoacetate, NaH, DCM; b...
  
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5. Scheme 3: Proposed mechanism of the Pd-catalyzed azide substitution of 6a in protic solvent.
  
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6. Scheme 4: Approach towards peracetylated D-IdoNAc 2c, reactions and conditions: a) Ti(OiPr)₄, t-BuOOH, D-DET,...
  
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Beilstein J. Org. Chem. 2018, 14, 856–860, doi:10.3762/bjoc.14.71

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One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone–sulfuric acid

Natalia Soldatova,
Pavel Postnikov,
Olga Kukurina,
Viktor V. Zhdankin,
Akira Yoshimura,
Thomas Wirth and
Mekhman S. Yusubov

Full Research Paper
Published 12 Apr 2018

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1. Graphical Abstract
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Beilstein J. Org. Chem. 2018, 14, 849–855, doi:10.3762/bjoc.14.70

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Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies

Elias Christoforides,
Andreas Papaioannou and
Kostas Bethanis

Full Research Paper
Published 11 Apr 2018

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1. Graphical Abstract
2. Figure 1: Schematic representation of (a) the cholesterol molecule; (b) the β-cyclodextrin molecule.
  
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3. Figure 2: (a) Crystal structure of the inclusion compound of cholesterol in β-CD dimer. Water molecules are o...
  
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4. Figure 3: RMSD over time for all CHL (green) and β-CD (blue) atoms (a) at 300 K and (b) at 340 K.
  
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5. Figure 4: Representative snapshots of the CHL/β-CD inclusion complex at 0 (a, c) and 11 ns (b, d) in timescal...
  
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6. Figure 5: (a) Distance between the O1 atom (CHL) and the centroid D_K of the O4n atoms of host A at 300 (green...
  
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Beilstein J. Org. Chem. 2018, 14, 838–848, doi:10.3762/bjoc.14.69

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Phosphodiester models for cleavage of nucleic acids

Satu Mikkola,
Tuomas Lönnberg and
Harri Lönnberg

Review
Published 10 Apr 2018

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1. Graphical Abstract
2. Figure 1: Enzymatic cleavage of phosphodiester linkages of DNA and RNA.
  
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3. Figure 2: Energy profiles for a concerted A_ND_N (A) and stepwise mechanisms (A_N + D_N) with rate-limiting break...
  
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4. Figure 3: Pseudorotation of a trigonal bipyramidal phosphorane intermediate by Berry pseudorotation [20].
  
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5. Figure 4: Protolytic equilibria of phosphorane intermediate of RNA transesterification.
  
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6. Figure 5: Structures of acyclic analogs of ribonucleosides.
  
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7. Figure 6: First-order rate constants for buffer-independent partial reactions of uridyl-3´,5´-uridine at pH 5...
  
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8. Scheme 1: pH- and buffer-independent cleavage and isomerization of RNA phosphodiester linkages. Observed firs...
  
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9. Scheme 2: Mechanism for the pH- and buffer-independent cleavage of RNA phosphodiester linkages.
  
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10. Scheme 3: Hydroxide-ion-catalyzed cleavage of RNA phosphodiester linkages.
  
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11. Scheme 4: Anslyn's and Breslow's mechanism for the buffer-catalyzed cleavage and isomerization of RNA phospho...
  
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12. Scheme 5: General base-catalyzed cleavage of RNA phosphodiester bonds.
  
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13. Scheme 6: Kirby´s mechanism for the buffer-catalyzed cleavage of RNA phosphodiester bonds [65].
  
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14. Figure 7: Guanidinium-group-based cleaving agents of RNA.
  
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15. Scheme 7: Tautomers of triazine-based cleaving agents and cleavage of RNA phosphodiester bonds by these agent...
  
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16. Figure 8: Bifunctional guanidine/guanidinium group-based cleaving agents of RNA.
  
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17. Scheme 8: Cleavage of HPNP by 1,3-distal calix[4]arene bearing two guanidine groups [80].
  
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18. Figure 9: Cyclic amine-based cleaving agents of RNA.
  
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19. Scheme 9: Mechanism for the pH-independent cleavage and isomerization of model compound 12a in the pH-range 7...
  
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20. Scheme 10: Mechanism for the pH-independent cleavage of guanylyl-3´,3´-(2´-amino-2´-deoxyuridine) at pH 6-8 [89].
  
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21. Scheme 11: Cleavage of uridine 3´-dimethyl phosphate by A) intermolecular attack of methoxide ion and B) intra...
  
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22. Scheme 12: Transesterification of group I introns and hydrolysis of phosphotriester models proceed through a s...
  
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23. Scheme 13: Cleavage of trinucleoside 3´,3´,5´-monophosphates by A) P–O3´ and B) P–O5´ bond fission.
  
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24. Figure 10: Model compounds (23–25) and metal ion binding ligands used in kinetic studies of metal-ion-promoted...
  
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25. Figure 11: Zn²⁺-ion-based mono- and di-nuclear cleaving agents of nucleic acids.
  
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26. Figure 12: Miscellaneous complexes and ligands used in kinetic studies of metal-ion-promoted cleavage of nucle...
  
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27. Figure 13: Azacrown ligands 34 and 35 and dinuclear Zn²⁺ complex 36 used in kinetic studies of metal-ion-promo...
  
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28. Figure 14: Metal ion complexes used for determination of β_lg values of metal-ion-promoted cleavage of RNA mode...
  
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29. Figure 15: Metal ion complexes used in kinetic studies of medium effects on the cleavage of RNA model compound...
  
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30. Scheme 14: Alternative mechanisms for metal-ion-promoted cleavage of phosphodiesters.
  
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31. Figure 16: Nucleic acid cleaving agents where the attacking oxyanion is not coordinated to metal ion.
  
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Beilstein J. Org. Chem. 2018, 14, 803–837, doi:10.3762/bjoc.14.68

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Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes

Zhensheng Zhao and
Graham K. Murphy

Letter
Published 09 Apr 2018

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1. Graphical Abstract
2. Scheme 1: Reactions of substituted allenes with HVI reagents.
  
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3. Scheme 2: Chlorination of p-tolylallene (2a) with (dichloroiodo)benzene (1a).
  
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4. Scheme 3: Chlorination of various aryl-substituted allenes. General conditions: Allene 2a (0.2 mmol, 1 equiv)...
  
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5. Scheme 4: Chlorination of various α-substituted phenylallene derivatives. General conditions: Allene 2a (0.2 ...
  
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6. Scheme 5: Chlorination of methoxy-substituted α-methyl phenylallenes. General conditions: Allene 2a (0.2 mmol...
  
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7. Scheme 6: Control reactions: (a) chlorination of deuterated biphenylallene [D₂]-2b; (b) reaction with TEMPO.
  
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8. Figure 1: Proposed reaction mechanism.
  
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Beilstein J. Org. Chem. 2018, 14, 796–802, doi:10.3762/bjoc.14.67

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Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: synthesis of axitinib

Jingbo Yu,
Zikun Hong,
Xinjie Yang,
Yu Jiang,
Zhijiang Jiang and
Weike Su

Full Research Paper
Published 06 Apr 2018

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1. Graphical Abstract
2. Scheme 1: Representative pharmaceutically useful indazoles.
  
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3. Scheme 2: Model Heck reaction of 3-bromo-N-methyl-1H-indazole (1a) and n-butyl acrylate (2a). (173 stainless-...
  
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4. Figure 1: Investigation of additives in the Heck reaction: 1a (1.5 mmol), 2a (2.25 mmol), Pd(OAc)₂ (5 mol %),...
  
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5. Scheme 3: The control experiments. ^aTEA (1.8 mmol), silica gel (5.0 g), ^bPd(OAc)₂ (5 mol %), PPh₃ (10 mol %),...
  
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6. Scheme 4: Plausible reaction pathway.
  
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7. Figure 2: Influence of milling time and rotation speed on the Heck reaction: 1a (1.5 mmol), 2a (2.25 mmol), P...
  
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8. Figure 3: Influence of the milling ball filling degree with different size on the Heck reaction: 1a (1.5 mmol...
  
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9. Scheme 5: Examination of the substrate scope. Reaction conditions: 1 (1.5 mmol), 2 (2.25 mmol), Pd(OAc)₂ (5 m...
  
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10. Scheme 6: Synthesis of axitinib by mechanochemical Heck–Migita coupling. Reagents and conditions: (i) NBS, Na...
  
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Beilstein J. Org. Chem. 2018, 14, 786–795, doi:10.3762/bjoc.14.66

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Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

Kartik Temburnikar and
Katherine L. Seley-Radtke

Review
Published 05 Apr 2018

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1. Graphical Abstract
2. Figure 1: Structural components of nucleic acids. Shown is the monomeric building block of nucleic acids. Cha...
  
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3. Figure 2: Formation of oxocarbenium ion during glycosidic bond cleavage in nucleosides [31]. The extent of leavin...
  
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4. Figure 3: Structural modifications to nucleobase-sugar connectivity. The O–C–N bond between nucleobase and su...
  
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5. Figure 4: Examples of natural and synthetic C-nucleosides. Pseudouridine and formcycin are among several natu...
  
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6. Figure 5: Synthetic approaches to C-nucleosides. A. Two common strategies for C-nucleoside synthesis involve ...
  
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7. Figure 6: Steroselective C-nucleoside synthesis using D-ribonolactone. A. Nucleophilic substitution of D-ribo...
  
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8. Figure 7: Synthesis of C1'-substituted 4-aza-7,9-dideazaadenine C-nucleosides [63-65,69,70]. A. Reaction of D-ribonolacton...
  
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9. Figure 8: Pyrrolo- and imidazo[2,1-f][1,2,4]triazine C-nucleosides. A series of sugar- and nucleobase-substit...
  
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10. Figure 9: Synthesis of 1',2'-cyclopentyl C-nucleoside [73]. Functional groups at C1' and C2' were installed and e...
  
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11. Figure 10: Anti-influenza C-nucleosides mimicking favipiravir riboside [74]. A. Structure of favipiravir and its r...
  
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12. Figure 11: Alternative method for synthesis of 2'-substituted C-nucleosides [75]. A. Synthesis of C2'-substituted ...
  
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13. Figure 12: Synthesis of carbocyclic C-nucleosides using cyclopentanone [53]. A. Nucleophlic substitution on cyclop...
  
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14. Figure 13: Synthesis of carbocyclic C-nucleosides via Suzuki coupling [53]. A. Synthesis of OTf-cyclopentene that ...
  
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Beilstein J. Org. Chem. 2018, 14, 772–785, doi:10.3762/bjoc.14.65

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Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery

Sabine Schuster,
Beáta Biri-Kovács,
Bálint Szeder,
Viktor Farkas,
László Buday,
Zsuzsanna Szabó,
Gábor Halmos and
Gábor Mező

Full Research Paper
Published 04 Apr 2018

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1. Graphical Abstract
2. Scheme 1: Syntheses of GnRH-III–[(⁴Lys(Bu)/⁴Ser, ⁶Aaa, ⁸Lys(Dau=Aoa)] bioconjugates. a) (1) 2% hydrazine in D...
  
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3. Figure 1: Far-UV ECD spectra of GnRH-III and its drug conjugates in water (GnRH-III solid, K1 dash, K2 dot, 1...
  
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4. Figure 2: Degradation of the GnRH-III bioconjugates by rat liver lysosomal homogenate. A) Cleavage sites prod...
  
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5. Figure 3: Cytostatic effect of the GnRH-III bioconjugates at different concentrations on A) HT-29 and B) MCF-...
  
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6. Figure 4: Cellular uptake of the GnRH-III bioconjugates at different concentrations on A) HT-29 and B) MCF-7 ...
  
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7. Figure 5: Cellular uptake of bioconjugate K2 (40 µM) visualized by confocal laser scanning microscopy (CLSM) ...
  
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8. Figure 6: Competitive inhibition of the GnRH-R on MCF-7 cells. Cellular uptake of the GnRH-III bioconjugate K2...
  
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Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64

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An uracil-linked hydroxyflavone probe for the recognition of ATP

Márton Bojtár,
Péter Zoltán Janzsó-Berend,
Dávid Mester,
Dóra Hessz,
Mihály Kállay,
Miklós Kubinyi and
István Bitter

Full Research Paper
Published 03 Apr 2018

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1. Graphical Abstract
2. Figure 1: Structures of the studied hydroxyflavone derivatives.
  
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3. Figure 2: Optimized geometries for (a) DEHF∙ATP, (b) UHF∙ATP with the adenine of ATP “sandwiched” between the...
  
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4. Scheme 1: Synthesis of UHF. (i) 4-Dimethylaminobenzaldehyde, DMF, NaOMe, rt, 17 h, (ii) hydrogen peroxide, Na...
  
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5. Figure 3: Variation of fluorescence spectra of UHF (1.0 μM) upon addition of increasing amounts of ATP in 0.0...
  
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6. Figure 4: Excitation spectra of UHF (dark green line, 1 μM) and UHF + 300 equiv ATP (red line), measured at d...
  
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7. Figure 5: Fluorescence enhancement (F/F₀) values of UHF (1.0 μM) upon addition of different nucleotides at 54...
  
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8. Figure 6: Ratio of the fluorescence intensities at 540 nm, the samples were excited at 470 and 400 nm. The re...
  
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Beilstein J. Org. Chem. 2018, 14, 747–755, doi:10.3762/bjoc.14.63

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Volatiles from the xylarialean fungus Hypoxylon invadens

Jeroen S. Dickschat,
Tao Wang and
Marc Stadler

Full Research Paper
Published 29 Mar 2018

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1. Graphical Abstract
2. Figure 1: Structures of the widespread fungal volatiles oct-1-en-3-ol (1) and 6-pentyl-2H-pyran-2-one (2), th...
  
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3. Figure 2: Total-ion chromatogram of the bouquet from Hypoxylon invadens MUCL 54175 obtained by the CLSA heads...
  
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4. Figure 3: Identified volatile organic compounds from Hypoxylon invadens MUCL 54175.
  
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5. Figure 4: Mass spectra of volatiles from Hypoxylon invadens MUCL 54175. Mass spectra of A) 2,5-dimethylphenol...
  
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6. Scheme 1: Proposed common biosynthetic pathway to volatile aromatic compounds from Hypoxylon invadens.
  
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7. Scheme 2: Synthesis of 5-hydroxy-2-methyl-4H-chromen-4-one (19).
  
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Beilstein J. Org. Chem. 2018, 14, 734–746, doi:10.3762/bjoc.14.62

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Nanoreactors for green catalysis

M. Teresa De Martino,
Loai K. E. A. Abdelmohsen,
Floris P. J. T. Rutjes and
Jan C. M. van Hest

Review
Published 29 Mar 2018

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1. Graphical Abstract
2. Figure 1: Assembly of catalyst-functionalized amphiphilic block copolymers into polymer micelles and vesicles...
  
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3. Scheme 1: C–N bond formation under micellar catalyst conditions, no organic solvent involved. Adapted from re...
  
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4. Scheme 2: Suzuki−Miyaura couplings with, or without, ppm Pd. Conditions: ArI 0.5 mmol 3a, Ar’B(OH)₂ (0.75–1.0...
  
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5. Figure 2: PQS (4a), PQS attached proline catalyst 4b. Adapted from reference [26]. Copyright 2012 American Chemic...
  
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6. Figure 3: 3a) Schematic representation of a Pickering emulsion with the enzyme in the water phase (i), or wit...
  
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7. Scheme 3: Cascade reaction with GOx and Myo. Adapted from reference [82].
  
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8. Figure 4: Cross-linked polymersomes with Cu(OTf)₂ catalyst. Reprinted with permission from [15].
  
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9. Figure 5: Schematic representation of enzymatic polymerization in polymersomes. (A) CALB in the aqueous compa...
  
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10. Figure 6: Representation of DSN-G₀. Reprinted with permission from [100].
  
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11. Figure 7: The multivalent esterase dendrimer 5 catalyzes the hydrolysis of 8-acyloxypyrene 1,3,6-trisulfonate...
  
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12. Figure 8: Conversion of 4-NP in five successive cycles of reduction, catalyzed by Au@citrate, Au@PEG and Au@P...
  
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Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

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Cobalt-catalyzed directed C–H alkenylation of pivalophenone N–H imine with alkenyl phosphates

Wengang Xu and
Naohiko Yoshikai

Full Research Paper
Published 28 Mar 2018

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1. Graphical Abstract
2. Scheme 1: Cobalt–NHC-catalyzed C–H alkenylation reactions with alkenyl electrophiles.
  
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3. Scheme 2: Reaction of substituted pivalophenone N–H imines with 2a. ^aThe major regioisomer is shown (rr = reg...
  
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4. Scheme 3: Reaction of 1a with various alkenyl phosphates. ^aA mixture of E- and Z-alkenyl phosphate (ca. 1:1) ...
  
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5. Scheme 4: The cyclization of o-alkenylpivalophenone N–H imine.
  
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6. Scheme 5: Proposed catalytic cycle (R = t-BuCH₂, R' = P(O)(OEt)₂).
  
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Beilstein J. Org. Chem. 2018, 14, 709–715, doi:10.3762/bjoc.14.60

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Stepwise radical cation Diels–Alder reaction via multiple pathways

Ryo Shimizu,
Yohei Okada and
Kazuhiro Chiba

Letter
Published 27 Mar 2018

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1. Graphical Abstract
2. Scheme 1: Radical cation Diels–Alder reaction of trans-anethole [17].
  
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3. Scheme 2: Radical cation Diels–Alder reactions of aryl vinyl ether and sulfides [17,25].
  
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4. Scheme 3: Radical cation Diels–Alder reaction of aryl vinyl ether (1). Conditions: 1.0 M LiClO₄/CH₃NO₂, carbo...
  
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5. Scheme 4: Oxidative SET-triggered reaction of aryl vinyl ether 1_c. Conditions: 1.0 M LiClO₄/CH₃NO₂, carbon fe...
  
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6. Figure 1: GC–MS Monitoring of the oxidative SET-triggered reaction of aryl vinyl ether 1_c.
  
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7. Scheme 5: Oxidative SET-triggered rearrangement of vinyl cyclobutane 4. Conditions: 1.0 M LiClO₄/CH₃NO₂, carb...
  
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8. Scheme 6: Unsuccessful rearrangement of cyclobutanes. Conditions: 1.0 M LiClO₄/CH₃NO₂, carbon felt electrodes...
  
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9. Scheme 7: Proposed mechanism for the radical cation Diels–Alder reaction of aryl vinyl ether 1.
  
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Beilstein J. Org. Chem. 2018, 14, 704–708, doi:10.3762/bjoc.14.59

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Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

Morten M. C. H. van Schie,
Tiago Pedroso de Almeida,
Gabriele Laudadio,
Florian Tieves,
Elena Fernández-Fueyo,
Timothy Noël,
Isabel W. C. E. Arends and
Frank Hollmann

Letter
Published 26 Mar 2018

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1. Graphical Abstract
2. Scheme 1: Enzymatic reaction schemes for the selective oxidation of trans-hex-2-enol. A: Alcohol dehydrogenas...
  
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3. Figure 1: Michaelis–Menten kinetics of the PeAAOx-catalysed oxidation of trans-hex-2-enol. Conditions: 50 mM ...
  
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4. Figure 2: The influence of the residence time on the conversion of trans-hex-2-enol (red squares) to trans-2-...
  
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5. Figure 3: Increasing the PeAAOx turnover numbers (TN) by increasing the residence time. Conditions: 6 mL flow...
  
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Beilstein J. Org. Chem. 2018, 14, 697–703, doi:10.3762/bjoc.14.58

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Liquid-assisted grinding and ion pairing regulates percentage conversion and diastereoselectivity of the Wittig reaction under mechanochemical conditions

Kendra Leahy Denlinger,
Lianna Ortiz-Trankina,
Preston Carr,
Kingsley Benson,
Daniel C. Waddell and
James Mack

Full Research Paper
Published 23 Mar 2018

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1. Graphical Abstract
2. Figure 1: Solution-based Wittig reaction mechanism.
  
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3. Figure 2: ¹H NMR spectra of stilbene mixture (a) and benzyl benzoate (b).
  
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4. Scheme 1: Possible mechanism of benzyl benzoate formation.
  
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5. Scheme 2: A possible mechanistic explanation for the E selectivity.
  
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6. Scheme 3: Ball-milled Wittig reaction using excess benzaldehyde.
  
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7. Figure 3: Comparison of solution based Wittig reaction (a) with polymer-supported mechanochemical Wittig reac...
  
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8. Scheme 4: Stepwise ball-milled Wittig reaction with ethanol as the LAG solvent.
  
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9. Scheme 5: Stepwise ball-milled Wittig reaction with ethanol evaporation between the steps.
  
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