Table of Contents
5	Full Research Paper
1	Review
3	Letter
2	Editorial

Combining the best of both worlds: radical-based divergent total synthesis

Kyriaki Gennaiou,
Antonios Kelesidis,
Maria Kourgiantaki and
Alexandros L. Zografos

Review
Published 02 Jan 2023

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1. Graphical Abstract
2. Scheme 1: The power of radical retrosynthesis and the tactic of divergent total synthesis.
  
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3. Figure 1: Evolution of radical chemistry for organic synthesis.
  
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4. Scheme 2: Divergent total synthesis of α-pyrone-diterpenoids (Baran).
  
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5. Scheme 3: Divergent synthesis of pyrone diterpenoids by merged chemoenzymatic and radical synthesis (part I, ...
  
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6. Scheme 4: Divergent synthesis of pyrone diterpenoids by merged chemoenzymatic and radical synthesis (part II,...
  
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7. Scheme 5: Divergent synthesis of drimane-type hydroquinone meroterpenoids (Li).
  
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8. Scheme 6: Divergent synthesis of natural products isolated from Dysidea avara (Lu).
  
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9. Scheme 7: Divergent synthesis of kaurene-type terpenoids (Lei).
  
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10. Scheme 8: Divergent synthesis of 6-oxabicyclo[3.2.1]octane meroterpenoids (Lou).
  
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11. Scheme 9: Divergent synthesis of crinipellins by radical-mediated Dowd–Backwith rearrangement (Xie and Ding).
  
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12. Scheme 10: Divergent total synthesis of Galbulimima alkaloids (Shenvi).
  
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13. Scheme 11: Divergent synthesis of eburnane alkaloids (Qin).
  
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14. Scheme 12: Divergent synthesis of Aspidosperma alkaloids (Boger).
  
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15. Scheme 13: Photoredox based synthesis of (−)-FR901483 (160) and (+)-TAN1251C (162, Gaunt).
  
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16. Scheme 14: Divergent synthesis of bipolamines (Maimone).
  
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17. Scheme 15: Flow chemistry divergency between aporphine and morphinandione alkaloids (Felpin).
  
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18. Scheme 16: Divergent synthesis of pyrroloazocine natural products (Echavarren).
  
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19. Scheme 17: Using TEMPO to stabilize radicals for the divergent synthesis of pyrroloindoline natural products (...
  
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20. Scheme 18: Radical pathway for preparation of lignans (Zhu).
  
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21. Scheme 19: Divergent synthesis of DBCOD lignans (Lumb).
  
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Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

Full Text

Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation

Julian Spils,
Thomas Wirth and
Boris J. Nachtsheim

Letter
Published 03 Jan 2023

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1. Graphical Abstract
2. Scheme 1: Synthesis of acyclic (DIS) and cyclic (CDIS) diaryliodonium salts.
  
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3. Figure 1: Substrate scope using the optimized conditions of Table 3. Yield is based on collecting for 3 h 20 min (2....
  
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Beilstein J. Org. Chem. 2023, 19, 27–32, doi:10.3762/bjoc.19.2

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Modern flow chemistry – prospect and advantage

Philipp Heretsch

Editorial
Published 06 Jan 2023

Beilstein J. Org. Chem. 2023, 19, 33–35, doi:10.3762/bjoc.19.3

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Improving the accuracy of ³¹P NMR chemical shift calculations by use of scaling methods

William H. Hersh and
Tsz-Yeung Chan

Full Research Paper
Published 10 Jan 2023

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1. Graphical Abstract
2. Figure 1: Training set of tri- and tetracoordinate phosphorus compounds; chemical shifts are in ppm, referenc...
  
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3. Figure 2: (a) Plot of experimental vs calculated chemical shifts of tri- and tetracoordinate phosphorus compo...
  
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4. Figure 3: Plot of experimental vs calculated chemical shifts of training set compounds reported by Latypov et...
  
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5. Figure 4: “Large” compounds selected for ³¹P NMR calculation by Latypov [37].
  
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6. Figure 5: Stereoisomers and unusual phosphorus compounds used for chemical shift calculations.
  
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7. Figure 6: Phosphorus-catalyzed oxygen transfer reaction intermediates.
  
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8. Figure 7: Phosphirane reactions.
  
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9. Figure 8: (a) Plot of experimental vs scaled chemical shifts derived from the tri- and tetracoordinate phosph...
  
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Beilstein J. Org. Chem. 2023, 19, 36–56, doi:10.3762/bjoc.19.4

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NaI/PPh₃-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

Dan Liu,
Yue Zhao and
Frederic W. Patureau

Letter
Published 16 Jan 2023

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1. Graphical Abstract
2. Figure 1: Representative natural products and biologically active molecules containing an oxindole moiety [7-13].
  
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3. Scheme 1: Selected photocatalytic decarboxylative radical cascade reactions of N-arylamides.
  
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4. Scheme 2: Arylamide substrate scope with isolated yields of products.
  
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5. Scheme 3: Alkyl radical precursor scope with isolated yields of products.
  
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6. Scheme 4: Selected mechanistic experiments.
  
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Beilstein J. Org. Chem. 2023, 19, 57–65, doi:10.3762/bjoc.19.5

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Catalytic aza-Nazarov cyclization reactions to access α-methylene-γ-lactam heterocycles

Bilge Banu Yagci,
Selin Ezgi Donmez,
Onur Şahin and
Yunus Emre Türkmen

Full Research Paper
Published 17 Jan 2023

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1. Graphical Abstract
2. Scheme 1: Examples of aza-Nazarov reactions.
  
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3. Scheme 2: Aza-Nazarov cyclization on gram scale.
  
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4. Scheme 3: Scope of the aza-Nazarov cyclization with acyclic imines. ^aThe syntheses of aza-Nazarov products 19b...
  
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5. Figure 1: X-ray crystal structure of compound 19l.
  
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6. Scheme 4: Proposed mechanism for the formation of diastereomers 19 and 22.
  
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7. Scheme 5: Preparation of acyl chloride 23.
  
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8. Scheme 6: Aza-Nazarov reaction tested using β-TMS-substituted acyl chloride 23.
  
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9. Scheme 7: Hydrolysis of N-acyliminium intermediates.
  
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10. Scheme 8: (a) Two possible pathways for the formation of 7 and (b) investigation of the reaction between imin...
  
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11. Scheme 9: (a) Preparation of acyl chlorides 6ba and 6bb in diastereomerically pure forms, (b) aza-Nazarov cyc...
  
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Beilstein J. Org. Chem. 2023, 19, 66–77, doi:10.3762/bjoc.19.6

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Preparation of β-cyclodextrin/polysaccharide foams using saponin

Max Petitjean and
José Ramón Isasi

Full Research Paper
Published 24 Jan 2023

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1. Graphical Abstract
2. Figure 1: Quillaja saponin foamability (left) and foam stability over time for the β-cyclodextrin/polysacchar...
  
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3. Figure 2: SEM images of crushed β-c-LBG as a function of the synthesis pathways (see below, Experimental sect...
  
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4. Figure 3: SEM of β-c_sp after crosslinking with or without washing the sample.
  
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5. Figure 4: β-c_sp (left) and c-CS_sp (right) matrices unwashed showing the “foam-like” morphologies.
  
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6. Figure 5: Values (in mg/g) of equivalent ‘free β-cyclodextrin’ in the polysaccharide (PS) matrices, as a func...
  
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7. Figure 6: 1-Naphthol isotherms of crosslinked β-cyclodextrin/polysaccharides (blue curves for chitosan, red f...
  
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8. Figure 7: Sorption of phenols (V, vanillin; Ph, phenol; m-c, m-cresol; 4eP, 4-ethylphenol; Eu, eugenol) in β-...
  
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9. Figure 8: Six synthesis routes (*lyophilized matrices) used to prepare samples β-c-XG_sp; β-c-LBG_sp; β-c-CS_sp ...
  
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Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

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Organophosphorus chemistry: from model to application

György Keglevich

Editorial
Published 25 Jan 2023

Beilstein J. Org. Chem. 2023, 19, 89–90, doi:10.3762/bjoc.19.8

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Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

Christian Schumacher,
Jas S. Ward,
Kari Rissanen,
Carsten Bolm and
Mohamed Ramadan El Sayed Aly

Full Research Paper
Published 27 Jan 2023

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1. Graphical Abstract
2. Figure 1: Chemical structure of three isomeric cholesterols.
  
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3. Figure 2: Selected previously described cholesterol derivatives with interesting antibacterial and cytotoxic ...
  
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4. Scheme 1: Stereochemical outcome of OH/N₃ transformations under different conditions.
  
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5. Figure 3: Top: cholesterol (1) and the less polar product from the Appel reaction, cholesta-3,5-diene (9); bo...
  
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6. Figure 4: Top: the more polar product from the Appel reaction 3β-bromocholest-5-ene (4); bottom: X-ray struct...
  
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7. Figure 5: Top: 3α-azidocholest-5-ene (5) obtained by treatment of 4 with NaN₃ in DMF; bottom: X-ray crystal s...
  
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8. Scheme 2: Mechanistic interpretation of the conversion of cholesterol 1 into diene 9, bromide 4, and azides 5...
  
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9. Figure 6: Compounds (next to 4, 5 and 9) to be corrected in refs. [10] and [11]. The respective bonds are highlighted...
  
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Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

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Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade

Qian-Ci Gao,
Yi-Fei Li,
Jun Xuan and
Xiao-Qiang Hu

Letter
Published 30 Jan 2023

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1. Graphical Abstract
2. Scheme 1: Significance of isocoumarins (a), classic methods for the synthesis of isocoumarins (b) and reactio...
  
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3. Scheme 2: Scope of enaminones.
  
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4. Scheme 3: Scope of iodonium ylides.
  
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5. Scheme 4: Gram-scale reaction (a) and synthetic transformation (b).
  
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6. Scheme 5: Proposed mechanism.
  
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Beilstein J. Org. Chem. 2023, 19, 100–106, doi:10.3762/bjoc.19.10

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Synthesis and characterisation of new antimalarial fluorinated triazolopyrazine compounds

Kah Yean Lum,
Jonathan M. White,
Daniel J. G. Johnson,
Vicky M. Avery and
Rohan A. Davis

Full Research Paper
Published 31 Jan 2023

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1. Graphical Abstract
2. Scheme 1: Synthesis of ether triazolopyrazine derivatives 4–9.
  
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3. Scheme 2: Synthesis of fluorinated triazolopyrazine compounds (10–18) via Diversinate™ chemistry.
  
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4. Figure 1: Key HMBC, COSY and ROESY correlations, and ORTEP drawing of 18.
  
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Supp. Info

Beilstein J. Org. Chem. 2023, 19, 107–114, doi:10.3762/bjoc.19.11

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Volume No. 19

2023

Pages 1 - 114

Table of Contents

Combining the best of both worlds: radical-based divergent total synthesis

Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation

Modern flow chemistry – prospect and advantage

Improving the accuracy of ³¹P NMR chemical shift calculations by use of scaling methods

NaI/PPh₃-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

Catalytic aza-Nazarov cyclization reactions to access α-methylene-γ-lactam heterocycles

Preparation of β-cyclodextrin/polysaccharide foams using saponin

Organophosphorus chemistry: from model to application

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade

Synthesis and characterisation of new antimalarial fluorinated triazolopyrazine compounds

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