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8 article(s) from Opatz, Till

Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt

Tobias Lucas,
Jule-Philipp Dietz and
Till Opatz

Full Research Paper
Published 20 Mar 2020

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1. Graphical Abstract
2. Figure 1: The structures of 5-fluorouracil (1), 5-fluorocytosine (2), emtricitabine (3) and capecitabine (4).
  
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3. Scheme 1: Synthesis of potassium (Z)-2-cyano-2-fluoroethenolate (8) by Dietz et al. [36].
  
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4. Scheme 2: Scope of the cyclization reaction. All yields are those of the purified products. ^aNo further purif...
  
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5. Scheme 3: Cyclization with phenylhydrazine (12a) to obtain the desired pyrazole 13a and the byproducts 13b an...
  
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Beilstein J. Org. Chem. 2020, 16, 445–450, doi:10.3762/bjoc.16.41

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A new member of the fusaricidin family – structure elucidation and synthesis of fusaricidin E

Marcel Reimann,
Louis P. Sandjo,
Luis Antelo,
Eckhard Thines,
Isabella Siepe and
Till Opatz

Full Research Paper
Published 20 Jul 2017

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1. Graphical Abstract
2. Figure 1: Structure of fusaricidins E (1) and F (2).
  
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3. Figure 2: NOESY /COSY and HMBC correlations of compound 1.
  
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4. Figure 3: Fragmentation pattern of compounds 1 and 2.
  
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5. Scheme 1: Retrosynthetic plan for the depsipeptide and GHPD side chain.
  
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6. Scheme 2: a) LiAlH₄, THF, reflux, 12 h, quant.; b) Fmoc-OSu, NaHCO₃, 1,4-dioxane, H₂O, 0 °C to rt, 87%; c) 1:...
  
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7. Scheme 3: Ester bond formation with 2,2-dimethylated pseudoproline including peptide 16.
  
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8. Scheme 4: Cyclization with 2,2-dimethylated pseudoproline including peptide 16.
  
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9. Scheme 5: Depsipeptide cyclization and coupling with GHPD side chain.
  
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10. Figure 4: Byproducts from removal of Cbz group in THF and DMF.
  
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Beilstein J. Org. Chem. 2017, 13, 1430–1438, doi:10.3762/bjoc.13.140

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Characterization of the synthetic cannabinoid MDMB-CHMCZCA

Carina Weber,
Stefan Pusch,
Dieter Schollmeyer,
Sascha Münster-Müller,
Michael Pütz and
Till Opatz

Full Research Paper
Published 21 Dec 2016

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1. Graphical Abstract
2. Figure 1: Synthetic cannabinoids JWH-018 (1), MDMB-CHMICA (2), MDMB-CHMCZCA (3), and EG-018 (4).
  
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3. Figure 2: Molecular structure of (S)-MDMB-CHMCZCA (3) with numbering scheme.
  
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4. Figure 3: ESI-MSⁿ pattern of 3 (m/z values) with probable fragment ion structures.
  
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5. Figure 4: Observed (top) and calculated (bottom) ECD spectra for (S)-3 in acetonitrile, theory level: TD-B3LY...
  
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6. Figure 5: Observed (top) and calculated (bottom) VCD spectra for (S)-3 in chloroform, theory level: B3PW91/6-...
  
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7. Figure 6: Molecular structure of (S)-3 in the solid state at 110 K (ORTEP-ellipsoids drawn at 30% probability...
  
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8. Figure 7: UV traces (254 nm) of the chiral HPLC for commercial (S)-3 (top) and the (R/S)-3 (bottom). t_R = 6.8...
  
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Beilstein J. Org. Chem. 2016, 12, 2808–2815, doi:10.3762/bjoc.12.279

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Chromatographically separable rotamers of an unhindered amide

Mario Geffe,
Lars Andernach,
Oliver Trapp and
Till Opatz

Full Research Paper
Published 21 Mar 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis of formamide 4. Reagents and conditions: a) KHMDS, THF, −78 °C; then: NaBH₄, MeOH, 63%. b...
  
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3. Figure 1: Equilibration of the Z-rotamer of 4 at 293 K.
  
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4. Figure 2: Equilibration of the E-rotamer of 4 at 293 K.
  
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5. Figure 3: Elution profiles obtained by temperature-dependent DHPLC measurements of 4.
  
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6. Figure 4: Eyring plot obtained by temperature dependent DHPLC measurements of 4.
  
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7. Figure 5: Potential energy surface scan graph for the dihedral angle O–C–N–C1 () in 4 (BP-D3/def2-SVP).
  
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8. Figure 6: Energy differences and geometries for E- and Z-4 and both transition states (TS1 and TS2) in hexane...
  
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Beilstein J. Org. Chem. 2014, 10, 701–706, doi:10.3762/bjoc.10.63

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Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones

Murat Kucukdisli,
Dorota Ferenc,
Marcel Heinz,
Christine Wiebe and
Till Opatz

Full Research Paper
Published 24 Feb 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis and conversion of 3,4-dihydro-2H-pyrrole-2-carbonitriles 6.
  
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Beilstein J. Org. Chem. 2014, 10, 466–470, doi:10.3762/bjoc.10.44

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Tanzawaic acids I–L: Four new polyketides from Penicillium sp. IBWF104-06

Louis P. Sandjo,
Eckhard Thines,
Till Opatz and
Anja Schüffler

Full Research Paper
Published 22 Jan 2014

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1. Graphical Abstract
2. Figure 1: HMBC, COSY and NOESY correlations of compound 1.
  
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3. Figure 2: HMBC, COSY and NOESY correlations of compound 2.
  
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4. Figure 3: HMBC, COSY and NOESY correlations of compound 3.
  
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5. Figure 4: HMBC, COSY and NOESY correlations of compound 4.
  
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6. Figure 5: Structures of the isolated compounds.
  
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7. Figure 6: Crystal structures (ORTEP plot) of arohynapene A (5, left) and tanzawaic acid E (8, right). Thermal...
  
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Beilstein J. Org. Chem. 2014, 10, 251–258, doi:10.3762/bjoc.10.20

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SF002-96-1, a new drimane sesquiterpene lactone from an Aspergillus species, inhibits survivin expression

Silke Felix,
Louis P. Sandjo,
Till Opatz and
Gerhard Erkel

Full Research Paper
Published 13 Dec 2013

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1. Graphical Abstract
2. Figure 1: Structure of SF002-96-1.
  
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3. Figure 2: COSY (bold) and HMBC (arrow) correlations of SF002-96-1.
  
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4. Figure 3: NOESY correlations of SF002-96-1.
  
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5. Figure 4: Effect of SF002-96-1 on survivin promoter activity, survivin mRNA levels and expression. (A) Colo 3...
  
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6. Figure 5: Effect of SF002-96-1 on Sat3 and NF-κB binding to the survivin promoter in Colo 320 cells analyzed ...
  
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7. Figure 6: SF002-96-1 induces apoptosis of Colo 320 cells. (A) Colo 320 cells were treated without (control) o...
  
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8. Figure 7: Single-quadrupole mass spectrumof SF002-96-1 obtained using an atmospheric pressure chemical ioniza...
  
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Beilstein J. Org. Chem. 2013, 9, 2866–2876, doi:10.3762/bjoc.9.323

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Screening of ligands for the Ullmann synthesis of electron-rich diaryl ethers

Nicola Otto and
Till Opatz

Full Research Paper
Published 17 Jul 2012

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1. Graphical Abstract
2. Figure 1: Selected examples of bioactive natural diaryl ethers.
  
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3. Figure 2: Ligands that were subjected to the ligand screening.
  
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4. Figure 3: Conversions of the model reaction versus the ligand numbers. For structures of the ligands refer to ...
  
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Beilstein J. Org. Chem. 2012, 8, 1105–1111, doi:10.3762/bjoc.8.122

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