Publications XG

50. Insights into the Enantioselective Au(I)-Catalyzed Reactions between 2-Alkynyl Ketones and Naphthols using the TCDC approach 

Yunliang Yu, Meriem Daghmoum, Nazarii Sabat, Zhenhao Zhang, Gilles Frison,*Angela Marinetti* and Xavier Guinchard* 2024 Submitted. .

 

49. Radical S-Adenosyl-l-Methionine Enzyme PylB: A C-Centered Radical to Convert l-Lysine into (3R)-3-Methyl-d-Ornithineas 

Feryel Soualmia, Mickael V. Cherrier, Timothée Chauviré, Mickaël Mauger, Philip Tatham, Alain Guillot, Xavier Guinchard, Lydie Martin, Patricia Amara, Jean-Marie Mouesca, Meriem Daghmoum, Alhosna Benjdia, Serge Gambarelli*, Olivier Berteau*, and Yvain Nicolet* J. Am. Chem. Soc.  2024. ASAP.

https://pubs.acs.org/doi/abs/10.1021/jacs.3c03747

 

48. Spiroindoles as Intermediates/Products in Transition Metal Catalyzed Dearomatization of Indoles Floris Buttard*, Xavier Guinchard*  ACS Catal.  2023. 13, 9442.

https://pubs.acs.org/doi/abs/10.1021/acscatal.3c01417

Also available on ChemRxiv: https://chemrxiv.org/engage/chemrxiv/article-details/64023ca19789de3dd9de35f5

47. Enantioselective Au(i)-catalyzed tandem reactions between 2-alkynyl enones and naphthols by the tethered counterion-directed catalysis strategy  Yunliang Yu, Nazarii Sabat, Meriem Daghmoum, Zhenhao Zhang,  Pascal Retailleau, Gilles Frison,*Angela Marinetti,* and Xavier Guinchard*  Org. Chem. Front. 2023. 10, 2936  # These authors contributed equally.

http://dx.doi.org/10.1039/D3QO00415E

Also available on ChemRxiv https://chemrxiv.org/engage/chemrxiv/article-details/63b449fab9c5f60d39e915c5

46.  Unbiased C3-Electrophilic Indoles: Triflic Acid Mediated C3-Regioselective Hydroarylation of N-H Indoles ;Sabat, N.#; Zhou, W.#; Gandon, V.; Guinchard, X.*; Vincent, G.*  Angew. Chem. Int. Ed. 2022, e202200627. # These authors contributed equally.

DOI https://onlinelibrary.wiley.com/doi/10.1002/anie.202204400  

Also available on ChemRxiv 

https://www.inc.cnrs.fr/fr/cnrsinfo/modifier-la-reactivite-de-lindole-pour-decouvrir-de-nouveaux-medicaments

45.  Exploring the Biosynthetic Potential of TsrM, a B12-dependent Radical SAM Methyltransferase Catalyzing Non-radical Reactions Soualmia, F.;Guillot, A.; Sabat, N.; Brewee, C.; Koubiak, X.; Haumann, M.; Guinchard, X.; Benjdia, A.; Berteau, O.  Chem. Eur. J. 2022, e202200627.

DOI 10.1002/chem.202200627

44. Enantioselective Au(I)-Catalyzed Multicomponent Annulation via Tethered Counterion-Directed Catalysis Zhang, Z.; Sabat, N.; Frison, G.; Marinetti, A.*; Guinchard, X.* ACS Catal. 2022, 12, 4046.

DOI 10.1021/acscatal.2c00120

Also available in ChemRxiv. 2021. link

43. Enantioselective Au(I)-Catalyzed Dearomatization of 1-Naphthols with Allenamides through Tethered Counterion-Directed Catalysis Yu, Y.; Zhang, Z.; Voituriez, A.; Rabasso, N.; Frison, G.; Marinetti, A.*; Guinchard, X.* Chem Commun. 2021, ASAP.
DOI 10.1039/D1CC04088J

42. Gold-Catalyzed Carboamination of Allenes by Tertiary Amines Proceeding with Benzylic Group Migration Milcendeau, P.; Gandon, V.*; Guinchard, X.* Adv. Synth. Catal. 2021, 363, 2893.

DOI 10.1002/adsc.202100007 .

Freely available in ChemRxiv

41. Au(I)-catalyzed Pictet-Spengler Reactions all around the indole ring Milcendeau, P.; Zhang, Z.; Glinsky-Olivier, N.; van Elslande, E.; Guinchard, X.* J. Org. Chem. 2021, 86, 9, 6406.

DOI 10.1021/acs.joc.1c00270

Freely available in ChemRxiv

40. Gold-Catalyzed Enantioselective Functionalizations of Indoles Milcendeau, P.; Sabat, N.; Ferry, A.*; Guinchard, X.*, Org. Biomol. Chem. 2020, 18, 6006.

DOI 10.1039/D0OB01245A

39. Chiral Phosphathiahelicenes: Improved Synthetic Approach and Uses in Enantioselective Gold(I)-Catalyzed [2+2] Cycloadditions of N-Homoallenyl Tryptamines. Magné, V. ; Sanogo, Y; Demmer, C. S.; Retailleau, P. ; Marinetti, A. ; Guinchard, X.*; Voituriez, A. * , ACS Catal., 2020, 10, 8141.

DOI 10.1021/acscatal.0c01819

 

38. Gold-Catalyzed Spirocyclization Reactions of N-Propargyl Tryptamines and Tryptophans in Aqueous Media. Sabat, N.; Soulamia, F.; Retailleau, P.; Benjdia, A.; Berteau, O.; Guinchard, X.* Org. Lett. 2020, 22, 4344.

DOI 10.1021/acs.orglett.0c01370

Also accessible freely : ChemRxiv. 2020DOI 10.26434/chemrxiv.12136782.v1

 

37. Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis. Zhang, Z.; Smal, V.; Retailleau, P.; Voituriez, A.; Frison, G.; Marinetti, A.*; Guinchard, X.* J. Am. Chem. Soc. 2020, 142, 3797.

DOI 10.1021/jacs.9b11154

 

36. Enantioselective Au(I)-Catalyzed Pictet-Spengler Reacations. Glinsky-Olivier, N.; Shengwen, Y.; Retailleau, P.; Gandon, V.* ; Guinchard, X.* Org. Lett. 2019, 21, 9446.
DOI : 10.1021/acs.orglett.9b03656

35. Reactions Involving Tryptamines and δ-Allenyl Aldehydes : Competition between Pictet-Spengler Reaction and Cyclization to 1-Aminotetralins. Gobé, V. ; Gandon, V.* ; Guinchard, X.* Adv. Synth. Catal. 2018, 360, 1280.
DOI : 10.1002/adsc.201701487

34. Gold-Catalyzed Synthesis of Spirofused Indoloquinuclidines. Glinsky-Olivier, N. ; Retailleau, P. ; Guinchard, X.* Eur. J. Org. Chem. 2018, doi:10.1002/ejoc.201800357.
DOI : 10.1002/ejoc.201800357

33. Gold-Catalyzed Synthesis of 2-Sulfenylspiroindolenines via Spirocyclizations. Magné, V. ; Retailleau, P. ; Marinetti, A. ; Voituriez, A Guinchard, X.* Molbank. 2018, M985.
DOI : 10.3390/M985

32. Dissecting the Gold(I)-Catalyzed Carboaminations of N-Allyl Tetrahydro-β-carbolines to Allenes. Gobé, V. ; Dousset, M. ; Retailleau, P. ; Gandon, V. ; Guinchard, X.* J. Org. Chem. 2018, 83, 898.
DOI : 10.1021/acs.joc.7b02900

31. Enantioselective Catalytic Methods for the Elaboration of Chiral Tetrahydro-β-carbolines and Related Scaffolds. Glinsky-Olivier, N. ; Guinchard, X.* Synthesis 2017, 49, 2605.
DOI : 10.1055/-s-0036-1589003

30. Synthesis of Spiroindolenines via Regioselective Gold(I)-Catalyzed Cyclizations of N-Propargyl Tryptamines. Magné, V. ; Marinetti, A. ; Gandon, V.* ; Voituriez, A. ; Guinchard, X.* Adv. Synth. Catal. 2017, 359, 4036.
DOI : 10.1002/adsc.201700932

29. Short Enantioselective Total Synthesis of (−)-Rhazinilam Using a Gold(I)-Catalyzed Cyclization. Magné, V. ; Lorton, C. ; Marinetti, A. ; Guinchard, X. ; Voituriez, A.* Org. Lett. 2017, 19, 4794-4797.
DOI : 10.1021/acs.orglett.7b02210

28. Synthesis of Spiro[piperidine-3,3’-oxindoles] via Gold(I)-Catalyzed Dearomatization of N-Propargyl- and N-Homoallenyl-2-bromotryptamines. Magné, V. ; Blanchard, F. ; Marinetti, A. ; Voituriez, A.* ; Guinchard, X.* Adv. Synth. Catal. 2016, 358, 3355-3361.
DOI : 10.1002/adsc.201600398

27. Gold(I)-Catalyzed Carboaminations of Allenes by N-Allyltetrahydro-β-carbolines : An Experimental and Theoretical Study. Gobé, V. ; Dousset, M. ; Retailleau, P. ; Gandon, V.* ; Guinchard, X.* Adv. Synth. Catal. 2016, 358, 3960-3965.
DOI : 10.1002/adsc.201601075

26. Self-Relay Gold(I)-Catalyzed Pictet-Spengler/Cyclization Cascade Reaction for the Rapid Elaboration of Pentacyclic Indole Derivatives. Gobé, V. ; Guinchard, X.* Chem. Eur. J. 2015, 21, 17587-17590.
DOI : 10.1002/chem.201503941

25. When Phosphosugars Meet Gold : Synthesis and Catalytic Activities of Phostones and Polyhydroxylated Phosphonite Au(I) Complexes. Malik, G. ; Ferry, A. ; Guinchard, X.* Molecules 2015, 20, 21082-21093. Open-access article :
DOI : doi:10.3390/molecules201219755

24. Stereoselective Synthesis of Chiral Polycyclic Indolic Architectures via Pd(0)-Catalysed Tandem Deprotection/Cyclization of Tetrahydro-β-carbolines on Allenes. Gobé, V. ; Guinchard, X.* Chem. Eur. J. 2015, 21, 8511-8520.
DOI : 10.1002/chem.201500273

23. Domino Formation of Enamines – Intramolecular Cyclizations to 1-Aminotetralins from γ-Arylallene Aldehydes and Amines. Gobé, V. ; Retailleau, P. ; Guinchard, X.* Org. Lett. 2014, 16, 5438-5441.
DOI : 10.1021/ol5026712

22. Thiophostone-Derived Brønsted Acids in the Organocatalyzed Transfer Hydrogenation of Quinolines : Influence of the P-Stereogenicity. Ferry, A. ; Stemper, J. ; Marinetti, A. ; Voituriez, A.* ; Guinchard, X.* Eur. J. Org. Chem. 2014, 188-193.

DOI : 10.1002/ejoc.201301253

21. Pd(0)-Catalyzed Tandem Deprotection/Cyclization of Tetrahydro-β-carbolines on Allenes : Application to the Synthesis of Indolo[2,3-a]quinolizidines. Gobé, V. ; Guinchard, X.* Org. Lett. 2014, 16, 1924-1927.
DOI : 10.1021/ol500448j

20. Synthesis and Evaluation of Di- and Trimeric Hydroxylamine-Based β-(1→3)-Glucan Mimetics. Ferry, A. ; Malik, G. ; Guinchard, X. ; Vetvicka, V. ; Crich, D. J. Am. Chem. Soc. 2014, 136, 14852-14857.
DOI : 10.1021/ja507084t

19. Alternative Synthesis of P-Chiral Phosphonite-Borane Complexes : Application to the Synthesis of Phostone–Phostone Dimers. Ferry, A. ; Malik, G. ; Retailleau, P. ; Guinchard, X. ; Crich, D. J. Org. Chem. 2013, 78, 6858-6867.
DOI : 10.1021/jo400864s

18. Synthesis of beta-Hydroxy O-Alkyl Hydroxylamines from Epoxides Using a Convenient and Versatile Two-Step Procedure. Malik, G. ; Ferry, A. ; Guinchard, X. ; Crich, D. Synthesis 2013, 45, 65-74.
DOI : 10.1055/s-0032-1317699

17. N-O Bond as a Glycosidic Bond Surrogate ; Synthetic Studies Toward Polyhydroxylated N-Alkoxypiperidines. Malik, G. ; Ferry, A. ; Guinchard, X. ; Crich, D. Chem. Eur. J. 2013, 19, 268-2179.
DOI : 10.1002/chem.201202374

16. Synthesis, Characterization and Coupling Reactions of Sixmembered Cyclic P-Chiral Ammonium Phosphonite-boranes ; Reactive H-Phosphinate Equivalents for the Stereoselective Synthesis of Glycomimetics. Ferry, A. ; Guinchard, X. ; Retailleau, P. ; Crich, D. J. Am. Chem. Soc. 2012, 134, 12289-12301.
DOI : 10.1021/ja305104b

15. 2-(Selenocyanatomethyl)-2-propenol. A Convenient Synthon for Ligation via the Deselenative Allylic Rearrangement of Allyl Selenosulfides : Preparation, Functional Group Compatibility and Application Lachkar, D. ; Boudet, C. ; Guinchard, X. ; Crich, D. Can. J. Chem. 2012, 90, 944-953.
DOI : 10.1139/v2012-056

14. Asymmetric Synthesis of Polyhydroxylated N-Alkoxypiperidines by Ring-Closing Double Reductive Amination : Facile Preparation of Isofagomine and Analogues. Malik, G. ; Guinchard, X. ; Crich, D. Org. Lett. 2012, 14, 596-599.
DOI : 10.1021/ol203213f

13. Study of the Total Synthesis of (-)-exiguolide. Cook, C. ; Liron, F. ; Guinchard, X. ; Roulland, E. J. Org. Chem. 2012, 77, 6728-6742.
DOI : 10.1021/jo301066p

12. Various Entries to Vinyl Chloride Derivatives and their Applications in Total Synthesis of Natural Products. Guinchard, X. ; Roulland, E. Synlett 2011, 2779-2788.
DOI : 10.1055/s-0031-1289862

11. Synthesis of the Landomycinone Skeleton. Bugaut, X. ; Guinchard, X. ; Roulland, E. J. Org. Chem. 2010, 75, 8190-8198.
DOI : 10.1021/jo1018377

10. Total Synthesis of (−)-Exiguolide. Cook, C. ; Guinchard, X. ; Liron, F. ; Roulland, E. Org. Lett. 2010, 12, 744-747.
DOI : 10.1021/ol902829e

9. Total Synthesis of the Antiproliferative Macrolide (+)-Neopeltolide. Guinchard, X. ; Roulland, E. Org. Lett. 2009, 11, 4700-4703.
DOI : 10.1021/ol902047z

8. Palladium(0)-Catalyzed Cross-Coupling of Potassium (Z)-2-Chloroalk-1-enyl Trifluoroborates : A Chemo- and Stereoselective Access to (Z)-Chloroolefins and Trisubstituted Alkenes. Guinchard, X. ; Bugaut, X. ; Cook, C. ; Roulland, E. Chem. Eur. J. 2009, 15, 5793-5798.
DOI : 10.1002/chem.200900425

7. Multigram Synthesis of a Water-Soluble Porphyrazine and Derived seco-Porphyrazine Labeling Agents. Guinchard, X. ; Fuchter, M. J. ; Ruggiero, A. ; Duckworth, B. J. ; Barrett, A. G. M. ; Hoffman, B. M. Org. Lett. 2007, 9, 5291-5294.
DOI : 10.1021/ol702481x

6. 1-(1H-Indol-3-yl)ethanamine Derivatives as Potent Staphylococcus aureus NorA Efflux Pump Inhibitors. Hequet, A. ; Burchak, O. N. ; Jeanty, M. ; Guinchard, X. ; Le Pihive, E. ; Maigre, L. ; Bouhours, P. ; Schneider, D. ; Maurin, M. ; Paris, J.-M. ; Denis, J.-N. ; Jolivalt, C. ChemMedChem 2014, 9, 1534-1545.
DOI : 10.1002/cmdc.201400042

5. Synthesis and evaluation of 1-(1H-indol-3-yl)ethanamine derivatives as new antibacterial agents. Burchak, O. N. ; Pihive, E. L. ; Maigre, L. ; Guinchard, X. ; Bouhours, P. ; Jolivalt, C. ; Schneider, D. ; Maurin, M. ; Giglione, C. ; Meinnel, T. ; Paris, J.-M. ; Denis, J.-N. Bioorg. & Med. Chem. 2011, 19, 3204-3215.
DOI : 10.1016/j.bmc.2011.03.060

4. Reactions of In Situ Generated N-Boc Nitrones with Aromatic and Heteroaromatic Grignard Reagents : Application to the Synthesis of Zileuton. Guinchard, X. ; Denis, J.-N. J. Org. Chem. 2008, 73, 2028-2031.
DOI : 10.1021/jo7025838

3. Total Synthesis of Marine Sponge Bis(indole) Alkaloids of the Topsentin Class. Guinchard, X. ; Vallée, Y. ; Denis, J.-N. J. Org. Chem. 2007, 72, 3972-3975.
DOI : 10.1021/jo070286r

2. Total Syntheses of Brominated Marine Sponge Alkaloids. Guinchard, X. ; Vallée, Y. ; Denis, J.-N. Org. Lett. 2007, 9, 3761-3764.
DOI : 10.1021/ol701626m

1. tert-Butyl (Phenylsulfonyl)alkyl- N-hydroxycarbamates :  The First Class of N-(Boc) Nitrone Equivalents. Guinchard, X. ; Vallée, Y. ; Denis, J.-N. Org. Lett. 2005, 7, 5147-5150.
DOI : 10.1021/ol051766c

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