Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin

Toni Smeilus,
Farnoush Mousavizadeh,
Johannes Krieger,
Xingzhao Tu,
Marcel Kaiser and
Athanassios Giannis

Full Research Paper
Published 27 Feb 2019

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1. Graphical Abstract
2. Figure 1: Structures of the natural (+)-artemisinin (1) and the synthesized (+)-3-hydroxymethylartemisinin (2...
  
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3. Scheme 1: Synthesis of the Diels–Alder precursor 8 over four steps in 71% yield, starting from aldehyde 3 and...
  
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4. Scheme 2: Synthesis of (+)-3-hydroxymethyl-9-desmethylartemisinin (16), starting from Diels–Alder derivatives ...
  
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5. Scheme 3: Synthesis of (+)-3-hydroxymethyl-9-epi-artemisinin (18) and (+)-3-hydroxymethylartemisinin (2). Rea...
  
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Beilstein J. Org. Chem. 2019, 15, 567–570, doi:10.3762/bjoc.15.51

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(2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues

Armin de Meijere,
Sergei I. Kozhushkov,
Dmitrii S. Yufit,
Christian Grosse,
Marcel Kaiser and
Vitaly A. Raev

Full Research Paper
Published 03 Dec 2014

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1. Graphical Abstract
2. Figure 1: Structure and absolute configuration of hormaomycin (1), its fluoromethyl-substituted analogues 8a–c...
  
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3. Figure 2: Structures of the Belokon'-type glycine complexes (BGC) (R)- and (S)-10.
  
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4. Scheme 1: Intended routes to methyl trans-2-(fluormethyl)cyclopropanecarboxylates 14a–c.
  
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5. Scheme 2: Synthesis of trans-(2-trifluoromethyl)cyclopropanecarboxylic acid (24).
  
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6. Scheme 3: Preparation of racemic trans-2-(fluoromethyl)cyclopropylmethyl iodides 11a–c and their conversion t...
  
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7. Figure 3: Structure and absolute configurations of the nickel(II) complexes (2S,1'R,2'S)-26a, (2S,1'R,2'S)-26b...
  
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8. Figure 4: Structure and absolute configuration of nickel(II) complex (R,R,R)-28 in the crystal. Hydrogen atom...
  
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9. Scheme 4: Mechanism of epimerization of the threonine nickel(II) complex 29.
  
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10. Scheme 5: A new general approach to (2S,3R)-β-methylarylalanines 3 by alkylation of the glycine nickel(II) co...
  
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11. Figure 5: Structure and absolute configuration of nickel(II) complex (2S,3S)-32 in the crystal. Hydrogen atom...
  
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12. Scheme 6: Synthesis of the cyclohexadepsipeptides 52a–c for the hormaomycin analogues 8a–c with 3-(2'-fluorom...
  
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13. Scheme 7: Synthesis of hormaomycin analogues with a: trifluoromethyl-, b: difluoromethyl-, c: monofluoromethy...
  
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14. Figure 6: Two derivatives 58 and 59 of cyclohexadepsipeptide 52a containing the (trifluoromethylcyclopropyl)a...
  
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Beilstein J. Org. Chem. 2014, 10, 2844–2857, doi:10.3762/bjoc.10.302

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Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

Friederike I. Nollmann,
Andrea Dowling,
Marcel Kaiser,
Klaus Deckmann,
Sabine Grösch,
Richard ffrench-Constant and
Helge B. Bode

Letter
Published 11 Apr 2012

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1. Graphical Abstract
2. Figure 1: Structure of depsipeptides szentiamide (1) [12] and xenematide (2) [8] identified in Xenorhabdus strains.
  
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3. Scheme 1: Overview of the synthetic strategy.
  
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4. Scheme 2: Synthesis of compound 1.
  
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5. Figure 2: HPLC–MS data of an XAD-extract of X. szentirmaii (a; base-peak chromatogram), the natural 1 (b; ext...
  
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Beilstein J. Org. Chem. 2012, 8, 528–533, doi:10.3762/bjoc.8.60

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Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin

(2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues

Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

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