Strong binding and fluorescence sensing of bisphosphonates by guanidinium-modified calix[5]arene

Jie Gao,
Zhe Zheng,
Lin Shi,
Si-Qi Wu,
Hongwei Sun and
Dong-Sheng Guo

Full Research Paper
Published 19 Jul 2018

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1. Graphical Abstract
2. Scheme 1: The chemical structures of (a) bisphosphonates (BPs) and (b) guanidinium-modified calix[5]arene (GC...
  
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3. Scheme 2: Schematic illustration of the binding between BPs and GC5A and the operating IDA principle of fluor...
  
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4. Scheme 3: The chemical structures of the selected BP drugs.
  
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5. Figure 1: (a) Fluorescence competitive titration of GC5A·Fl (0.9/1.0 μM) with risedronate (up to 29.6 μM) in ...
  
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6. Figure 2: The set-up calibration lines of the fluorescence intensities for quantitatively determining the con...
  
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Beilstein J. Org. Chem. 2018, 14, 1840–1845, doi:10.3762/bjoc.14.157

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First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

Grzegorz Mlostoń,
Katarzyna Urbaniak,
Paweł Urbaniak,
Anna Marko,
Anthony Linden and
Heinz Heimgartner

Full Research Paper
Published 19 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Reactions of aryl/hetarylthiochalcones 1a–d with 1,4-naphthoquinone (2b).
  
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3. Scheme 2: Reactions of thiochalcones 1a–d with 1,4-anthraquinones 2c and 2d.
  
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4. Figure 1: ORTEP plot [29] of the molecular structure of 4k showing the major conformation of the disordered thiop...
  
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5. Figure 2: Products of the reactions of thiochalcones 1a and 1b with 1,4-benzoquinone (2a) and of 1a with mena...
  
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Beilstein J. Org. Chem. 2018, 14, 1834–1839, doi:10.3762/bjoc.14.156

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Synthesis of new tricyclic 5,6-dihydro-4H-benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepine derivatives by [3⁺ + 2]-cycloaddition/rearrangement reactions

Lin-bo Luan,
Zi-jie Song,
Zhi-ming Li and
Quan-rui Wang

Full Research Paper
Published 18 Jul 2018

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1. Graphical Abstract
2. Figure 1: Examples of marketed pharmaceutical 1,2,4-triazolobenzodiazepines.
  
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3. Scheme 1: Preparation of N-acylated 2,3-dihydro-4(1H)-quinolones 6.
  
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4. Scheme 2: Synthesis of α-acetoxyazo compounds 8a–g. Reaction conditions: for synthesis of 8a: 7a (10.42 mmol)...
  
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5. Scheme 3: Synthesis of tricyclic benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepinium salts 10. Reaction conditions...
  
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6. Scheme 4: Synthesis of N(1)-unsubstituted benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepines 13. Reaction conditio...
  
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7. Scheme 5: Mechanistic rationale for the [3⁺ + 2]-cycloaddition/rearrangement reaction.
  
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8. Figure 2: Crystal structure of salt 10k. The displacement ellipsoids are drawn at the 30% probability level.
  
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9. Figure 3: Crystal structure of the free base 13e. The displacement ellipsoids are drawn at the 30% probabilit...
  
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Beilstein J. Org. Chem. 2018, 14, 1826–1833, doi:10.3762/bjoc.14.155

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Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

Xiang Li,
Pinhong Chen and
Guosheng Liu

Review
Published 18 Jul 2018

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1. Graphical Abstract
2. Figure 1: The structures of hypervalent iodine (III) reagents [8].
  
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3. Scheme 1: Hypervalent iodine(III)-catalyzed functionalization of alkenes.
  
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4. Scheme 2: Catalytic sulfonyloxylactonization of alkenoic acids [43].
  
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5. Scheme 3: Catalytic diacetoxylation of alkenes [46].
  
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6. Scheme 4: Intramolecular asymmetric dioxygenation of alkenes [48,50].
  
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7. Scheme 5: Intermolecular asymmetric diacetoxylation of styrenes [52].
  
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8. Scheme 6: Diacetoxylation of alkenes with ester groups containing catalysts 17 [55].
  
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9. Scheme 7: Intramolecular diamination of alkenes [56].
  
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10. Scheme 8: Intramolecular asymmetric diamination of alkenes [57].
  
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11. Scheme 9: Intermolecular asymmetric diamination of alkenes [58].
  
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12. Scheme 10: Iodoarene-catalyzed aminofluorination of alkenes [60,61].
  
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13. Scheme 11: Iodoarene-catalyzed aminofluorination of alkenes [62].
  
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14. Scheme 12: Catalytic difluorination of alkenes with Selectfluor [63].
  
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15. Scheme 13: Iodoarene-catalyzed 1,2-difluorination of alkenes [64].
  
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16. Scheme 14: Iodoarene-catalyzed asymmetric fluorination of styrenes [64,65].
  
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17. Scheme 15: Gem-difluorination of styrenes [67].
  
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18. Scheme 16: Asymmetric gem-difluorination of cinnamic acid derivatives [68].
  
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19. Scheme 17: Oxyarylation of alkenes [71].
  
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20. Scheme 18: Asymmetric oxidative rearrangements of alkenes [72].
  
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21. Scheme 19: Bromolactonization of alkenes [75].
  
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22. Scheme 20: Bromination of alkenes [77,78].
  
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23. Scheme 21: Cooperative strategy for the carbonylation of alkenes [79].
  
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Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

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Graphitic carbon nitride prepared from urea as a photocatalyst for visible-light carbon dioxide reduction with the aid of a mononuclear ruthenium(II) complex

Kazuhiko Maeda,
Daehyeon An,
Ryo Kuriki,
Daling Lu and
Osamu Ishitani

Full Research Paper
Published 17 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Synthesis of g-C₃N₄ by thermal heating of urea and application to photocatalytic CO₂ reduction with...
  
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3. Figure 1: XRD patterns of g-C₃N₄ synthesized at different temperatures. A broad peak at around 22 degree, ind...
  
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4. Figure 2: FTIR spectra of g-C₃N₄ synthesized at different temperatures. Each spectrum was acquired by a KBr m...
  
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5. Figure 3: TEM images of g-C₃N₄ synthesized at different temperatures.
  
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6. Figure 4: UV–visible diffuse reflectance spectra of g-C₃N₄ synthesized at different temperatures.
  
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7. Figure 5: A typical TEM image of Ag-loaded g-C₃N₄. The synthesis temperature of g-C₃N₄ was 873 K in this case....
  
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Beilstein J. Org. Chem. 2018, 14, 1806–1812, doi:10.3762/bjoc.14.153

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Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

Fateh V. Singh,
Priyanka B. Kole,
Saeesh R. Mangaonkar and
Samata E. Shetgaonkar

Review
Published 17 Jul 2018

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1. Graphical Abstract
2. Figure 1: The structures of biologically active natural and synthetic products having spirocyclic moiety.
  
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3. Scheme 1: Iodine(III)-mediated spirocyclization of substituted phenols 7 and 11 to 10 and 13, respectively.
  
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4. Scheme 2: PIDA-mediated spirolactonization of N-protected tyrosine 14 to spirolactone 16.
  
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5. Figure 2: The structures of polymer-supported iodine(III) reagents 17a and 17b.
  
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6. Scheme 3: Spirolactonization of substrates 14 to spirolactones 16 using polymer-supported reagents 17a and 17b...
  
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7. Scheme 4: PIDA-mediated spirolactonization of 1-(p-hydroxyaryl)cyclobutanols 18 to spirolactones 19.
  
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8. Scheme 5: Iodine(III)-mediated spirocyclization of aryl alkynes 24 to spirolactones 26 by the reaction with b...
  
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9. Scheme 6: Bridged iodine(III)-mediated spirocyclization of phenols 27 to spirodienones 29.
  
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10. Scheme 7: Iodine(III)-mediated spirocyclization of arnottin I (30) to its spirocyclic analogue arnottin II (32...
  
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11. Scheme 8: Iodine(III)-catalyzed spirolactonization of p-substituted phenols 27 to spirolactones 29 using iodo...
  
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12. Scheme 9: Iodine(III)-catalyzed oxylactonization of ketocarboxylic acid 34 to spirolactone 36 using iodobenze...
  
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13. Scheme 10: Iodine(III)-mediated asymmetric oxidative spirocyclization of naphthyl acids 37 to naphthyl spirola...
  
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14. Scheme 11: Oxidative cyclization of L-tyrosine 14 to spirocyclic lactone 16 using PIDA (15).
  
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15. Scheme 12: Oxidative cyclization of oxazoline derivatives 41 to spirolactams 42 using PIDA (15).
  
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16. Scheme 13: Oxidative cyclization of oxazoline 43 to spirolactam 44 using PIDA 15 as oxidant.
  
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17. Scheme 14: PIFA-mediated spirocyclization of amides 46 to N-spirolactams 47 using PIFA (31) as an electrophile....
  
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18. Scheme 15: Synthesis of spirolactam 49 from phenolic enamide 48 using PIDA (15).
  
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19. Scheme 16: Iodine(III)-mediated spirocyclization of alkyl hydroxamates 50 to spirolactams 51 using stoichiomet...
  
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20. Scheme 17: PIFA-mediated cyclization of substrate 52 to spirocyclic product 54.
  
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21. Scheme 18: Synthesis of spiro β-lactams 56 by oxidative coupling reaction of p-substituted phenols 55 using PI...
  
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22. Scheme 19: Iodine(III)-mediated spirocyclization of para-substituted amide 58 to spirolactam 59 by the reactio...
  
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23. Scheme 20: Iodine(III)-mediated synthesis of spirolactams 61 from anilide derivatives 60.
  
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24. Scheme 21: PIFA-mediated oxidative cyclization of anilide 60 to bis-spirobisoxindole 61.
  
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25. Scheme 22: PIDA-mediated spirocyclization of phenylacetamides 65 to spirocyclic lactams 66.
  
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26. Scheme 23: Oxidative dearomatization of arylamines 67 with PIFA (31) to give dieniminium salts 68.
  
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27. Scheme 24: PIFA-mediated oxidative spirocarbocyclization of 4-methoxybenzamide 69 with diphenylacetylene (70) ...
  
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28. Scheme 25: Synthesis of spiroxyindole 75 using I₂O₅/TBHP oxidative system.
  
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29. Scheme 26: Iodine(III)-catalyzed spirolactonization of functionalized amides 76 to spirolactones 77 using iodo...
  
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30. Scheme 27: Intramolecular cyclization of alkenes 78 to spirolactams 80 using Pd(II) 79 and PIDA (15) as the ox...
  
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31. Scheme 28: Iodine(III)-catalyzed spiroaminocyclization of amides 76 to spirolactam 77 using bis(iodoarene) 81 ...
  
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32. Scheme 29: Iodine(III)-catalyzed spirolactonization of N-phenyl benzamides 82 to spirolactams 83 using iodoben...
  
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33. Scheme 30: Iodine(III)-mediated asymmetric oxidative spirocyclization of phenols 84 to spirolactams 86 using c...
  
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34. Scheme 31: Iodine(III)-catalyzed asymmetric oxidative spirocyclization of N-aryl naphthamides 87 to spirocycli...
  
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35. Scheme 32: Cyclization of p-substituted phenolic compound 89 to spirolactam 90 using PIDA (15) in TFE.
  
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36. Scheme 33: Iodine(III)-mediated synthesis of spirocyclic compound 93 from substrates 92 using PIDA (15) as an ...
  
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37. Scheme 34: Iodine(III)-mediated spirocyclization of p-substituted phenol 48 to spirocyclic compound 49 using P...
  
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38. Scheme 35: Bridged iodine(III)-mediated spirocyclization of O-silylated phenolic compound 96 in the synthesis ...
  
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39. Scheme 36: PIFA-mediated approach for the spirocyclization of ortho-substituted phenols 98 to aza-spirocarbocy...
  
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40. Scheme 37: Oxidative cyclization of para-substituted phenols 102 to spirocarbocyclic compounds 104 using Koser...
  
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41. Scheme 38: Iodine(III)-mediated spirocyclization of aryl alkynes 105 to spirocarbocyclic compound 106 by the r...
  
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42. Scheme 39: Iodine(III)-mediated spirocarbocyclization of ortho-substituted phenols 107 to spirocarbocyclic com...
  
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43. Scheme 40: PIFA-mediated oxidative cyclization of substrates 110 to spirocarbocyclic compounds 111.
  
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44. Scheme 41: Iodine(III)-mediated cyclization of substrate 113 to spirocyclic compound 114.
  
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45. Scheme 42: Iodine(III)-mediated spirocyclization of phenolic substrate 116 to the spirocarbocyclic natural pro...
  
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46. Scheme 43: Iodine(III)-catalyzed spirocyclization of phenols 117 to spirocarbocyclic products 119 using iodoar...
  
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47. Scheme 44: PIFA-mediated spirocyclization of 110 to spirocyclic compound 111 using PIFA (31) as electrophile.
  
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48. Scheme 45: PIDA-mediated spirocyclization of phenolic sulfonamide 122 to spiroketones 123.
  
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49. Scheme 46: Iodine(III)-mediated oxidative spirocyclization of 2-naphthol derivatives 124 to spiropyrrolidines ...
  
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50. Scheme 47: PIDA-mediated oxidative spirocyclization of m-substituted phenols 126 to tricyclic spiroketals 127.
  
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51. Figure 3: The structures of chiral organoiodine(III) catalysts 129a and 129b.
  
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52. Scheme 48: Iodine(III)-catalyzed oxidative spirocyclization of substituted phenols 128 to spirocyclic ketals 1...
  
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53. Scheme 49: Oxidative spirocyclization of para-substituted phenol 131 to spirodienone 133 using polymer support...
  
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54. Scheme 50: Oxidative cyclization of bis-hydroxynaphthyl ether 135 to spiroketal 136 using PIDA (15) as an elec...
  
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55. Scheme 51: Oxidative spirocyclization of phenolic compound 139 to spirodienone 140 using polymer-supported PID...
  
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56. Scheme 52: PIFA-mediated oxidative cyclization of catechol derived substrate 142 to spirocyclic product 143.
  
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57. Scheme 53: Oxidative spirocyclization of p-substituted phenolic substrate 145 to aculeatin A (146a) and aculea...
  
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58. Scheme 54: Oxidative spirocyclization of p-substituted phenolic substrate 147 to aculeatin A (146a) and aculea...
  
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59. Scheme 55: Oxidative spirocyclization of p-substituted phenolic substrate 148 to aculeatin D (149) using elect...
  
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60. Scheme 56: Cyclization of phenolic substrate 131 to spirocyclic product 133 using polymer-supported PIFA 150.
  
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61. Scheme 57: Iodine(III)-mediated oxidative intermolecular spirocyclization of 7-methoxy-α-naphthol (152) to spi...
  
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62. Scheme 58: Oxidative cyclization of phenols 155 to spiro-ketals 156 using electrophilic species PIDA (15).
  
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63. Scheme 59: Iodine(III)-catalyzed oxidative spirocyclization of ortho-substituted phenols 158 to spirocyclic ke...
  
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Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152

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Defining the hydrophobic interactions that drive competence stimulating peptide (CSP)-ComD binding in Streptococcus pneumoniae

Bimal Koirala,
Robert A. Hillman,
Erin K. Tiwold,
Michael A. Bertucci and
Yftah Tal-Gan

Full Research Paper
Published 16 Jul 2018

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1. Graphical Abstract
2. Figure 1: The competence regulon QS circuitry in S. pneumoniae. ComC is processed and secreted by ComAB as th...
  
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3. Figure 2: Assessment of protein–peptide binding pockets. Key side-chain residues (black) can either fully occ...
  
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4. Figure 3: Design of CSP1 analogs. The CSP1 sequence is presented using the one-letter amino acid code. Residu...
  
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5. Figure 4: Helical wheel representation of CSP1. The CSP1 residues are presented using the one-letter amino ac...
  
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Beilstein J. Org. Chem. 2018, 14, 1769–1777, doi:10.3762/bjoc.14.151

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Synthesis and photophysical studies of a multivalent photoreactive Ru^II-calix[4]arene complex bearing RGD-containing cyclopentapeptides

Sofia Kajouj,
Lionel Marcelis,
Alice Mattiuzzi,
Adrien Grassin,
Damien Dufour,
Pierre Van Antwerpen,
Didier Boturyn,
Eric Defrancq,
Mathieu Surin,
Julien De Winter,
Pascal Gerbaux,
Ivan Jabin and
Cécile Moucheron

Full Research Paper
Published 16 Jul 2018

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1. Graphical Abstract
2. Figure 1: Targeted multivalent phototherapeutic agent and its calix[4]arene-based precursor. RGD = Arg–Gly–As...
  
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3. Scheme 1: Synthesis of Ru^II-calix[4]arene complex 7.
  
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4. Scheme 2: Synthesis of Ru^II-calix[4]arene-[c-(RGDfK)]₄ conjugate 9.
  
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5. Figure 2: MD snapshot showing an optimized model of conjugate 9. RGDfK units are depicted in orange ribbons, ...
  
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6. Figure 3: Absorption and emission spectra of Ru^II-calix[4]arene-[c-(RGDfK)]₄ conjugate 9 in water.
  
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7. Figure 4: Luminescence intensity and excited state lifetime of conjugate 9 in the presence of GMP measured in...
  
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8. Figure 5: Transient absorption spectra of Ru^II-calix[4]arene-[c-(RGDfK)]₄ conjugate 9 (in 10 mM Tris·HCl buff...
  
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9. Figure 6: MALDI–MS analysis of a solution containing conjugate 9 and GMP after continuous light irradiation. ...
  
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Beilstein J. Org. Chem. 2018, 14, 1758–1768, doi:10.3762/bjoc.14.150

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An amine protecting group deprotectable under nearly neutral oxidative conditions

Shahien Shahsavari,
Chase McNamara,
Mark Sylvester,
Emily Bromley,
Savannah Joslin,
Bao-Yuan Lu and
Shiyue Fang

Full Research Paper
Published 13 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Dmoc and dM-Dmoc protection and deprotection of amines.
  
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3. Scheme 2: Selective deprotection of dM-Dmoc-, Boc- and Fmoc-protected amines.
  
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Beilstein J. Org. Chem. 2018, 14, 1750–1757, doi:10.3762/bjoc.14.149

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DFT calculations on the mechanism of copper-catalysed tandem arylation–cyclisation reactions of alkynes and diaryliodonium salts

Tamás Károly Stenczel,
Ádám Sinai,
Zoltán Novák and
András Stirling

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Published 12 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Possible intermediates of the interaction of alkynyl compounds with Ar–Cu(III) species.
  
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3. Scheme 2: Two possible reaction routes for the oxazoline formation explored by computations. The schemes indi...
  
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4. Scheme 3: Free energy profiles for the possible reaction routes. The final energy state (−50.5 kcal/mol) is n...
  
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Beilstein J. Org. Chem. 2018, 14, 1743–1749, doi:10.3762/bjoc.14.148

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Synthesis of pyrimido[1,6-a]quinoxalines via intermolecular trapping of thermally generated acyl(quinoxalin-2-yl)ketenes by Schiff bases

Svetlana O. Kasatkina,
Ekaterina E. Stepanova,
Maksim V. Dmitriev,
Ivan G. Mokrushin and
Andrey N. Maslivets

Full Research Paper
Published 11 Jul 2018

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1. Graphical Abstract
2. Figure 1: Quinoxaline-based 6/6/6-angularly fused scaffolds and respective examples of biologically active co...
  
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3. Figure 2: Synthetic routes towards the pyrimido[1,6-a]quinoxaline scaffold.
  
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4. Figure 3: Acyl(quinoxalin-2-yl)ketene.
  
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5. Scheme 1: Thermolysis of five-membered 2,3-dioxoheterocycles resulting in acyl(quinoxalin-2-yl)ketenes.
  
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6. Figure 4: STA plot of thermolysis of PQT 1a. Blue solid curve: DSC; green solid curve: TG; greed dashed curve...
  
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7. Scheme 2: Side-reactions concurring with intermolecular trapping of ketene generated from PQT 1a by benzalani...
  
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8. Figure 5: Scope of the intermolecular trapping of ketenes generated from PQTs 1a–h by Schiff bases 2a–d under...
  
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9. Scheme 3: Formation of furoquinoxalines 6a,b via intramolecular cyclization in ketenes generated from PQTs 1g,...
  
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10. Figure 6: ORTEP drawing of compound 3g (CCDC 1834011) showing thermal ellipsoids at the 30% probability level....
  
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11. Figure 7: ORTEP drawing of compound 3j (CCDC 1834012) showing thermal ellipsoids at the 30% probability level....
  
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Beilstein J. Org. Chem. 2018, 14, 1734–1742, doi:10.3762/bjoc.14.147

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Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

Rakesh Puttreddy,
Ngong Kodiah Beyeh,
S. Maryamdokht Taimoory,
Daniel Meister,
John F. Trant and
Kari Rissanen

Full Research Paper
Published 10 Jul 2018

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1. Graphical Abstract
2. Figure 1: The chemical structures of C-ethyl-2-bromoresorcinarene (BrC2), C-propyl-2-bromoresorcinarene (BrC3...
  
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3. Figure 2: X-ray crystal structures of (a) 3@BrC6, (b) 4@BrC6, (c) 5@BrC6, (d) 6@BrC6, (e) 7@BrC6, (f) 8@BrC6,...
  
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4. Figure 3: Comparison of X-ray crystal structures (a) 3@BrC2, (c) 3@BrC3, and (e) 3@BrC6 and their DFT-based o...
  
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5. Figure 4: (a) The negative potential localised on the N-oxide oxygen in 3@BrC6 and, (b) the positive charge d...
  
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6. Figure 5: An expansion of the ¹H NMR (6.6 mM at 298 K, 500 MHz) of BrC6 complexes with 3. Spectra are produce...
  
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Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146

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Design, synthesis and structure of novel G-2 melamine-based dendrimers incorporating 4-(n-octyloxy)aniline as a peripheral unit

Cristina Morar,
Pedro Lameiras,
Attila Bende,
Gabriel Katona,
Emese Gál and
Mircea Darabantu

Full Research Paper
Published 09 Jul 2018

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1. Graphical Abstract
2. Figure 1: The key elements for design and construction of the targeted G-2 dendrimers.
  
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3. Scheme 1: Convergent versus divergent three steps (a–c) synthesis of central building blocks C1 and C3.
  
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4. Scheme 2: Synthesis of G-1 dendrons D-Cl and D-N<P>NH. *As partial conversions of 1 into 2a and 2b based on t...
  
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5. Scheme 3: Synthesis of G-2 dendrimers 4–6 by m-trimerisations of G-1 dendrons D-Cl and D-N<P>NH.
  
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6. Scheme 4: Synthesis of G-2 dendrimers 7–9 by m-trimerisations of G-1 dendron D-N<P>NH.
  
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7. Figure 2: The three terms rotamerism of G-0 dendrons 2a and 3 about the C(s-triazine)–N(exocyclic) partial do...
  
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8. Figure 3: Comparative details from ¹H NMR spectra of G-2 dendrimer 5 (500 MHz, 5.0 mM in DMSO-d₆).
  
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9. Figure 4: Comparative IR spectra (KBr) of compounds 7a vs 7b (a), 7b vs trimesic acid (b), 8 vs C1 (c) and 9 ...
  
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10. Figure 5: 2D-¹H-DOSY NMR charts (DMSO-d₆, 500 MHz, 298 K) of compounds 7a, 7b (2.5 mM), 8 and 9 (5.0 mM).
  
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11. Figure 6: The DFT optimised geometry at M062X/def2-TZVP level of theory of G-2 dendrimer 7a in DMSO (hydrogen...
  
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12. Figure 7: The DFT optimised geometry at M062X/def2-TZVP level of theory of trimesic tris-carboxylate anion (a...
  
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13. Figure 8: The DFT optimised geometry at M062X/def2-TZVP level of theory of G-2 dendrimers 8 and 9 in DMSO.
  
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14. Figure 9: TEM images of homogeneously packed spherical nano-aggregates (a) and their agglomerations (b) in th...
  
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15. Figure 10: TEM images of homogeneously packed spherical nano-aggregates (a) and their agglomerations (b) in th...
  
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16. Figure 11: Proposed π-stacking interactions in compounds D-N<P>NH and 5–7a.
  
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Beilstein J. Org. Chem. 2018, 14, 1704–1722, doi:10.3762/bjoc.14.145

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Natural and redesigned wasp venom peptides with selective antitumoral activity

Marcelo D. T. Torres,
Gislaine P. Andrade,
Roseli H. Sato,
Cibele N. Pedron,
Tania M. Manieri,
Giselle Cerchiaro,
Anderson O. Ribeiro,
Cesar de la Fuente-Nunez and
Vani X. Oliveira Jr.

Full Research Paper
Published 06 Jul 2018

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1. Graphical Abstract
2. Figure 1: Helical wheel projections of Dec-NH₂ and its analogs, where the yellow circles refer to the hydroph...
  
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3. Figure 2: MTT assays using Dec-NH₂ and its synthetic analogs after 2 and 24 h of exposure to MCF-7 cancer cel...
  
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4. Figure 3: MTT assays evaluating the toxicity of Dec-NH₂ and its derivatives towards MCF-10A normal cells afte...
  
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5. Figure 4: Cell death analysis using flow cytometry. Dot plot graphs from left to right, show cells treated wi...
  
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6. Figure 5: Topological images of untreated MCF-7 cells (A) and cells treated for 24 h with 50 μmol L⁻¹ of Dec-...
  
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Beilstein J. Org. Chem. 2018, 14, 1693–1703, doi:10.3762/bjoc.14.144

Full Text

β-Hydroxy sulfides and their syntheses

Mokgethwa B. Marakalala,
Edwin M. Mmutlane and
Henok H. Kinfe

Review
Published 05 Jul 2018

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1. Graphical Abstract
2. Figure 1: Some sulfur-containing natural products.
  
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3. Figure 2: Some natural products incorporating β-hydroxy sulfide moieties.
  
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4. Figure 3: Some synthetic β-hydroxy sulfides of clinical value.
  
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5. Scheme 1: Alumina-mediated synthesis of β-hydroxy sulfides, ethers, amines and selenides from epoxides.
  
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6. Scheme 2: β-Hydroxy sulfide syntheses by ring opening of epoxides under different Lewis and Brønsted acid and...
  
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7. Scheme 3: n-Bu₃P-catalyzed thiolysis of epoxides and aziridines to provide the corresponding β-hydroxy and β-...
  
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8. Scheme 4: Zinc(II) chloride-mediated thiolysis of epoxides.
  
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9. Scheme 5: Thiolysis of epoxides and one-pot oxidation to β-hydroxy sulfoxides under microwave irradiation.
  
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10. Scheme 6: Gallium triflate-catalyzed ring opening of epoxides and one-pot oxidation.
  
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11. Scheme 7: Thiolysis of epoxides and one-pot oxidation to β-hydroxy sulfoxides using Ga(OTf)₃ as a catalyst.
  
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12. Scheme 8: Ring opening of epoxide using ionic liquids under solvent-free conditions.
  
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13. Scheme 9: N-Bromosuccinimide-catalyzed ring opening of epoxides.
  
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14. Scheme 10: LiNTf₂-mediated epoxide opening by thiophenol.
  
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15. Scheme 11: Asymmetric ring-opening of cyclohexene oxide with various thiols catalyzed by zinc L-tartrate.
  
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16. Scheme 12: Catalytic asymmetric ring opening of symmetrical epoxides with t-BuSH catalyzed by (R)-GaLB (43) wi...
  
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17. Scheme 13: Asymmetric ring opening of meso-epoxides by p-xylenedithiol catalyzed by a (S,S)-(salen)Cr complex.
  
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18. Scheme 14: Desymmetrization of meso-epoxide with thiophenol derivatives.
  
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19. Scheme 15: Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by a C₂-symmetric chira...
  
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20. Scheme 16: Enantioselective ring-opening reaction of stilbene oxides with ArSH catalyzed by a C₂-symmetric chi...
  
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21. Scheme 17: Asymmetric desymmetrization of meso-epoxides using BINOL-based Brønsted acid catalysts.
  
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22. Scheme 18: Lithium-BINOL-phosphate-catalyzed desymmetrization of meso-epoxides with aromatic thiols.
  
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23. Scheme 19: Ring-opening reactions of cyclohexene oxide with thiols by using CPs 1-Eu and 2-Tb.
  
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24. Scheme 20: CBS-oxazaborolidine-catalyzed borane reduction of β-keto sulfides.
  
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25. Scheme 21: Preparation of β-hydroxy sulfides via connectivity.
  
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26. Scheme 22: Baker’s yeast-catalyzed reduction of sulfenylated β-ketoesters.
  
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27. Scheme 23: Sodium-mediated ring opening of epoxides.
  
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28. Scheme 24: Disulfide bond cleavage-epoxide opening assisted by tetrathiomolybdate.
  
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29. Scheme 25: Proposed reaction mechanism of disulfide bond cleavage-epoxide opening assisted by tetrathiomolybda...
  
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30. Scheme 26: Cyclodextrin-catalyzed difunctionalization of alkenes.
  
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31. Scheme 27: Zinc-catalyzed synthesis of β-hydroxy sulfides from disulfides and alkenes.
  
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32. Scheme 28: tert-Butyl hydroperoxide-catalyzed hydroxysulfurization of alkenes.
  
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33. Scheme 29: Proposed mechanism of the radical hydroxysulfurization.
  
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34. Scheme 30: Rongalite-mediated synthesis of β-hydroxy sulfides from styrenes and disulfides.
  
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35. Scheme 31: Proposed mechanism of Rongalite-mediated synthesis of β-hydroxy sulfides from styrenes and disulfid...
  
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36. Scheme 32: Copper(II)-catalyzed synthesis of β-hydroxy sulfides 15e,f from alkenes and basic disulfides.
  
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37. Scheme 33: CuI-catalyzed acetoxysulfenylation of alkenes.
  
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38. Scheme 34: CuI-catalyzed acetoxysulfenylation reaction mechanism.
  
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39. Scheme 35: One-pot oxidative 1,2-acetoxysulfenylation of Baylis–Hillman products.
  
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40. Scheme 36: Proposed mechanism for the oxidative 1,2-acetoxysulfination of Baylis–Hillman products.
  
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41. Scheme 37: 1,2-Acetoxysulfenylation of alkenes using DIB/KI.
  
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42. Scheme 38: Proposed reaction mechanism of the diacetoxyiodobenzene (DIB) and KI-mediated 1,2-acetoxysulfenylat...
  
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43. Scheme 39: Catalytic asymmetric thiofunctionalization of unactivated alkenes.
  
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44. Scheme 40: Proposed catalytic cycle for asymmetric sulfenofunctionalization.
  
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45. Scheme 41: Synthesis of thiosugars using intramolecular thiol-ene reaction.
  
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46. Scheme 42: Synthesis of leukotriene C-1 by Corey et al.: (a) N-(trifluoroacetyl)glutathione dimethyl ester (3 ...
  
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47. Scheme 43: Synthesis of pteriatoxins with epoxide thiolysis to attain β-hydroxy sulfides. Reagents: (a) (1) K₂...
  
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48. Scheme 44: Synthesis of peptides containing a β-hydroxy sulfide moiety.
  
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49. Scheme 45: Synthesis of diltiazem (12) using biocatalytic resolution of an epoxide followed by thiolysis.
  
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Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

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Synthesis of diamido-bridged bis-pillar[5]arenes and tris-pillar[5]arenes for construction of unique [1]rotaxanes and bis-[1]rotaxanes

Ying Han,
Li-Ming Xu,
Cui-Yun Nie,
Shuo Jiang,
Jing Sun and
Chao-Guo Yan

Full Research Paper
Published 04 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Synthesis of pillar[5]arene mono(oxyalkoxy)benzoic acids 3a–c.
  
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3. Figure 1: single crystal structure of pillar[5]arene 2a.
  
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4. Figure 2: Single crystal structure of pillar[5]arene 2f.
  
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5. Scheme 2: Synthesis of diamido-bridged bis-pillar[5]arenes 5a–d.
  
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6. Figure 3: The 2D NOSEY spectrum of bis-pillar[5]arene 5d.
  
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7. Scheme 3: Synthesis of pillar[5]arene di(oxyalkoxy)benzoic acid 8.
  
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8. Figure 4: Single crystal structure of pillar[5]arene 7.
  
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9. Scheme 4: Synthesis of diamido-bridged tris-pillar[5]arenes 9a–d.
  
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10. Figure 5: The 2D NOSEY spectra of tris-pillar[5]arene 9d.
  
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Beilstein J. Org. Chem. 2018, 14, 1660–1667, doi:10.3762/bjoc.14.142

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Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

Ugo Azzena,
Massimo Carraro,
Gloria Modugno,
Luisa Pisano and
Luigi Urtis

Letter
Published 03 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Synthesis of THP ether 3a.
  
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3. Scheme 2: Synthesis of THP ethers 3b–l in the presence of NH₄HSO₄@SiO₂. All reactions were run at rt, in the ...
  
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4. Scheme 3: Deprotection of THP ether 3i.
  
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5. Scheme 4: One-pot synthesis of 3-[4-(tetrahydro-2H-pyran-2-yl)oxymethylphenyl]-3-pentanol (4fa).
  
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6. Scheme 5: One-pot synthesis of 4-(tetrahydro-2H-pyran-2-yloxymethyl)benzyl alcohol (4fb).
  
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Beilstein J. Org. Chem. 2018, 14, 1655–1659, doi:10.3762/bjoc.14.141

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The phenyl vinyl ether–methanol complex: a model system for quantum chemistry benchmarking

Dominic Bernhard,
Fabian Dietrich,
Mariyam Fatima,
Cristóbal Pérez,
Hannes C. Gottschalk,
Axel Wuttke,
Ricardo A. Mata,
Martin A. Suhm,
Melanie Schnell and
Markus Gerhards

Full Research Paper
Published 02 Jul 2018

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1. Graphical Abstract
2. Figure 1: Minimum structures of the most stable PVE–MeOH dimers obtained at the B3LYP-D3(BJ)/def2-TZVP level;...
  
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3. Figure 2: Dispersion interaction density (DID) plots calculated at the LCCSD/VQZ-F12 level. The brown zones i...
  
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4. Figure 3: FTIR spectra of the supersonic expansion of methanol (MeOH) and phenyl vinyl ether (PVE) at differe...
  
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5. Figure 4: The IR/R2PI spectrum in the range of 3520–3750 cm⁻¹ was obtained via the excitation energy of 36885...
  
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6. Figure 5: A section of the experimental 2–8 GHz spectrum using a mixture of PVE and MeOH (3 million acquisiti...
  
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7. Figure 6: UV/IR/UV spectrum of PVE–MeOH in the range of 3520–3750 cm⁻¹; excitation laser: 36741 cm⁻¹, ionizin...
  
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Beilstein J. Org. Chem. 2018, 14, 1642–1654, doi:10.3762/bjoc.14.140

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Visible light-mediated difluoroalkylation of electron-deficient alkenes

Vyacheslav I. Supranovich,
Vitalij V. Levin,
Marina I. Struchkova,
Jinbo Hu and
Alexander D. Dilman

Letter
Published 02 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Fluoroalkylation of alkenes.
  
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3. Figure 1: Difluoroalkylation of alkenes. Isolated yields are shown. ^a2 equiv of the alkene were used.
  
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4. Scheme 2: Proposed mechanism.
  
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Beilstein J. Org. Chem. 2018, 14, 1637–1641, doi:10.3762/bjoc.14.139

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Anomeric modification of carbohydrates using the Mitsunobu reaction

Julia Hain,
Patrick Rollin,
Werner Klaffke and
Thisbe K. Lindhorst

Review
Published 29 Jun 2018

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1. Graphical Abstract
2. Scheme 1: Left: The Mitsunobu reaction is essentially a nucleophilic substitution of alcohols occurring with ...
  
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3. Scheme 2: Mechanistic considerations on the Mitsunobu reaction with carbohydrate hemiacetals (depicted in sim...
  
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4. Scheme 3: Anomeric esterification using the Mitsunobu procedure [29].
  
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5. Scheme 4: Conversion of allyl glucuronate into various 1-O-esterified allyl glucuronates using anomeric Mitsu...
  
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6. Scheme 5: Synthesis of anomeric glycosyl esters as substrates for Au-catalyzed glycosylation [40].
  
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7. Scheme 6: Correlation between pK_a value of the employed acids (or alcohol) and the favoured anomeric configur...
  
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8. Scheme 7: Synthesis of the β-mannosyl phosphates for the synthesis of HBP 43 by anomeric phosphorylation acco...
  
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9. Scheme 8: Synthesis of phenyl glycosides 44 and 45 from unprotected sugars [24].
  
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10. Scheme 9: Synthesis of azobenzene mannosides 47 and 48 without protecting group chemistry [46].
  
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11. Scheme 10: Synthesis of various aryl sialosides using Mitsunobu glycosylation [25].
  
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12. Scheme 11: Mitsunobu synthesis of different jadomycins [54,55]. BOM: benzyloxymethyl.
  
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13. Scheme 12: Stereoselectivity in the Mitsunobu synthesis of catechol glycosides in the gluco- and manno-series [56]....
  
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14. Scheme 13: Formation of a 1,2-cis glycoside 80 assisted by steric hindrance of the β-face of the disaccharide ...
  
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15. Scheme 14: Stereoselective β-D-mannoside synthesis [60].
  
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16. Scheme 15: TIPS-assisted synthesis of 1,2-cis arabinofuranosides [63]. TIPS: triisopropylsilyl.
  
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17. Scheme 16: The Mitsunobu reaction with glycals leads to interesting rearrangement products [69].
  
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18. Scheme 17: Synthesis of disaccharides using mercury(II) bromide as co-activator in the Mitsunobu reaction [75].
  
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19. Scheme 18: Synthesis of various fructofuranosides according to Mitsunobu and proposed neighbouring group parti...
  
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20. Scheme 19: The Mitsunobu reaction allows stereoslective acetalization of dihydroartemisinin [77].
  
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21. Scheme 20: Synthesis of alkyl thioglycosides by Mitsunobu reaction [81].
  
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22. Scheme 21: Preparation of iminoglycosylphthalimide 115 from 114 [85].
  
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23. Scheme 22: Mitsunobu reaction as a key step in the total synthesis of aurantoside G [87].
  
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24. Scheme 23: Utilization of an N–H acid in the Mitsunobu reaction [88].
  
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25. Scheme 24: Mitsunobu reaction with 1H-tetrazole [89].
  
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26. Scheme 25: Formation of a rebeccamycin analogue using the Mitsunobu reaction [101].
  
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27. Scheme 26: Synthesis of carbohydrates with an alkoxyamine bond [114].
  
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28. Scheme 27: Synthesis of glycosyl fluorides and glycosyl azides according to Mitsunobu [118,119].
  
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29. Scheme 28: Anomeric oxidation under Mitsunobu conditions [122].
  
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Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

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Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

Yuichi Yoshimura,
Hideaki Wakamatsu,
Yoshihiro Natori,
Yukako Saito and
Noriaki Minakawa

Review
Published 28 Jun 2018

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1. Graphical Abstract
2. Figure 1: Design of potential antineoplastic nucleosides.
  
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3. Scheme 1: Synthesis of 4’-thioDMDC.
  
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4. Scheme 2: Synthesis of 4’-thioribonucleosides by Minakawa and Matsuda.
  
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5. Scheme 3: Synthesis of 4’-thioribonucleosides by Yoshimura.
  
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6. Figure 2: Concept of the Pummerer-type glycosylation and hypervalent iodine-mediated glycosylation.
  
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7. Scheme 4: Oxidative glycosylation of 4-thioribose mediated by hypervalent iodine.
  
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8. Figure 3: Speculated mechanism of oxidative glycosylation mediated by hypervalent iodine.
  
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9. Scheme 5: Synthesis of purine 4’-thioribonucleosides using hypervalent iodine-mediated glycosylation.
  
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10. Scheme 6: Unexpected glycosylation of a thietanose derivative.
  
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11. Scheme 7: Speculated mechanism of the ring expansion of a thietanose derivative.
  
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12. Scheme 8: Synthesis of thietanonucleosides using the Pummerer-type glycosylation.
  
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13. Scheme 9: First synthesis of 4’-selenonucleosides.
  
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14. Scheme 10: The Pummerer-type glycosylation of 4-selenoxide 74.
  
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15. Scheme 11: Synthesis of purine 4’-selenonucleosides using hypervalent iodine-mediated glycosylation.
  
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16. Figure 4: Concept of the oxidative coupling reaction applicable to the synthesis of carbocyclic nucleosides.
  
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17. Scheme 12: Oxidative coupling reaction mediated by hypervalent iodine.
  
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18. Scheme 13: Synthesis of cyclohexenyl nucleosides using an oxidative coupling reaction.
  
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19. Figure 5: Concept of the oxidative coupling reaction of glycal derivatives.
  
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20. Scheme 14: Oxidative coupling reaction of silylated uracil and DHP using hypervalent iodine.
  
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21. Scheme 15: Proposed mechanism of the oxidative coupling reaction mediated by hypervalent iodine.
  
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22. Figure 6: Synthesis of 2’,3’-unsaturated nucleosides using hypervalent iodine and a co-catalyst.
  
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23. Scheme 16: Synthesis of dihydropyranonucleoside.
  
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24. Scheme 17: Synthesis of acetoxyacetals using hypervalent iodine and addition of silylated base.
  
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25. Scheme 18: One-pot fragmentation-nucleophilic additions mediated by hypervalent iodine.
  
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26. Figure 7: The reaction of thioglycoside with hypervalent iodine in the presence of Lewis acids.
  
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27. Scheme 19: Synthesis of disaccharides employing thioglycosides under an oxidative coupling reaction mediated b...
  
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28. Scheme 20: Synthesis of disaccharides using disarmed thioglycosides by hypervalent iodine-mediated glycosylati...
  
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29. Scheme 21: Glycosylation using aryl(trifluoroethyl)iodium triflimide.
  
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30. Figure 8: Expected mechanism of hypervalent iodine-mediated glycosylation with glycals.
  
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31. Scheme 22: Synthesis of oligosaccharides by hypervalent iodine-mediated glycosylation with glycals.
  
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32. Scheme 23: Synthesis of 2-deoxy amino acid glycosides.
  
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33. Figure 9: Rationale for the intramolecular migration of the amino acid unit.
  
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Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137

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Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

Livia Polgár,
Eszter Lajkó,
Pál Soós,
Orsolya Láng,
Marilena Manea,
Béla Merkely,
Gábor Mező and
László Kőhidai

Full Research Paper
Published 28 Jun 2018

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1. Graphical Abstract
2. Figure 1: Chemical structures of the GnRH-drug conjugates synthesized and investigated in the present work. A...
  
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3. Figure 2: Chemical structures of the bifunctional GnRH-drug conjugates synthesized and investigated in the pr...
  
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4. Figure 3: Long-term cytotoxic effects – impedimetrically registered negative effect on cell proliferation/via...
  
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5. Figure 4: Long-term cytotoxic effects – impedimetrically registered negative effect on cell proliferation and...
  
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Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

Full Text

Direct electrochemical generation of organic carbonates by dehydrogenative coupling

Tile Gieshoff,
Vinh Trieu,
Jan Heijl and
Siegfried R. Waldvogel

Full Research Paper
Published 27 Jun 2018

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1. Graphical Abstract
2. Figure 1: Current non-phosgene approaches to organic carbonates.
  
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3. Scheme 1: Preparation of tetrabutylammonium methyl carbonate by direct carbon dioxide incorporation.
  
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4. Scheme 2: Direct generation of mesityl methyl carbonate by dehydrogenative functionalization.
  
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5. Figure 2: Influence of the electrode distance; ^{a 1}H NMR yield; ^bisolated yield.
  
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Beilstein J. Org. Chem. 2018, 14, 1578–1582, doi:10.3762/bjoc.14.135

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A conformationally adaptive macrocycle: conformational complexity and host–guest chemistry of zorb[4]arene

Liu-Pan Yang,
Song-Bo Lu,
Arto Valkonen,
Fangfang Pan,
Kari Rissanen and
Wei Jiang

Full Research Paper
Published 27 Jun 2018

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1. Graphical Abstract
2. Scheme 1: (a) Chemical structures of ZB4 and the guests involved in this research. The counterions are PF₆⁻. ...
  
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3. Figure 1: X-ray single crystal structure of ZB4 and the host–guest complexes. a) ZB4, b) 2⁺@ZB4-IV, c) 3⁺@ZB4...
  
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4. Figure 2: Parabolic free-energy relationship between log(K_R/K_H) and Hammett parameter σ_p. K_R: guests 11⁺–21⁺; ...
  
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5. Figure 3: X-ray single crystal structures of 14⁺@ZB4-III, 16⁺@ZB4-III, 18⁺@ZB4-III and 21⁺@ZB4-III. Butyl gro...
  
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6. Figure 4: X-ray single crystal structures of 18⁺@ZB4-III and 18⁺ in 18⁺@ZB4-III.
  
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7. Figure 5: Linear relationships of ΔH with temperature (left, slope = −0.13, R² = 0.9956) and TΔS (right, slop...
  
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Beilstein J. Org. Chem. 2018, 14, 1570–1577, doi:10.3762/bjoc.14.134

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Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA

Timo Weinrich,
Eva A. Jaumann,
Ute M. Scheffer,
Thomas F. Prisner and
Michael W. Göbel

Full Research Paper
Published 26 Jun 2018

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1. Graphical Abstract
2. Figure 1: Structures of TEMPO-labeled oligonucleotides and of phosphoramidites 5–8.
  
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3. Scheme 1: Synthesis of phosphoramidite 5. Reagents and conditions: (a) 1. 2,4,6-triisopropylbenzenesulfonyl c...
  
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4. Scheme 2: Synthesis of phosphoramidite 7. Reagents and conditions: (a) Addition of 10, diisopropylethylamine,...
  
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5. Scheme 3: Synthesis of phosphoramidite 8. Reagents and conditions: (a) Addition of 10, diisopropylethylamine,...
  
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6. Figure 2: Structures of palindromic oligonucleotides prepared from amidites 5 (22a, 23a), 7 (24a, 25a), and 8...
  
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7. Figure 3: PELDOR measurement of 24c (12mer dA). The background-corrected time trace (original time trace in Supporting Information File 1,...
  
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