Institut de Chimie Moléculaire et des Matériaux d'Orsay

2023

• "Total Synthesis of Mavacuran Alkaloids via Bioinspired and Non-Bioinspired Strategies." C. Kouklovsky, E. Poupon,* L. Evanno,* G. Vincent* Synlett, 2023, doi:10.1055/s-0042-1751498 (account, cluster on "Biomimetic Synthesis")

.

• "Benzylic C–H arylation with dicyanoarenes via convergent paired electrolysis." S. Tang, G. Vincent* Green Chem., 2023, 25, 5483-5488.

                     

• "Collective Total Synthesis of Mavacuran Alkaloids through Intermolecular 1,4-Addition of an Organolithium Reagent." A. Mauger, M. Jarret, A. Tap, R. Perrin, R. Guillot, C. Kouklovsky, V. Gandon,* G. Vincent* Angew. Chem. Int. Ed., 2023, 62, e202302461.

                                  Communication from CNRS

                                  Highlighted in  Synfact, 2023, 19(6), 0534

2022

• "Total Synthesis of Ophiorrhine A, G and Ophiorrhiside E Featuring a Bioinspired Intramolecular Diels–Alder Cycloaddition" Wei, C.; Dou, Y.; Kouklovsky, C.; Vincent, G.* Angew. Chem. Int. Ed. 2022, 61, e202209135.

                       Highlighted in  “Organic Chemistry Portal“ web site.

• "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, 61, e202204400.

                                  Communication from CNRS

• "Electrochemical Benzylic C–H Functionalization with Isocyanides" Tang, S.; Guillot, R.; Grimaud, L.*; Vitale, M.*; Vincent, G.* Org. Lett. 2022, 24, 2125-2130.

• "Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition."  A. Rousseau, G. Vincent, C. Kouklovsky* Beilstein J. Org. Chem. 2022, 18, 1385-1395.

2021

• "Synthesis of a Seco iso-Secologanin Aglycone Analogue of Interest toward Secoiridoids and Monoterpene Indole Alkaloids" Abou-Hamdan, H.; Guillot, R.; Kouklovsky, C.; Vincent, G.* J. Org. Chem. 2021, 86, 9244-9252.

• "The Chemistry of Mavacurane Alkaloids: A Rich Source of Bis-Indole Alkaloids" Mauger, A.; Jarret, M.; Kouklovsky, C.; Poupon, E.*; Evanno, L.*; Vincent, G.* Nat. Prod. Rep. 2021 (review).

• "Bioinspired Early Divergent Oxidative Cyclizations toward Pleiocarpamine, Talbotine, and Strictamine" Jarret, M.; Abou-Hamdan, H.; Kouklovsky, C.; Poupon, E.; Evanno, L.; Vincent, G.* Org. Lett  2021, 23, 1355-1360.

 

• "Natural products originated from the oxidative coupling of tyrosine and tryptophan: biosynthesis and bioinspired synthesis" Tang, S.; Vincent, G.* Chem. Eur. J.  2021, 27, 2612-2622 (mini review).

 

• "Des molécules cycliques 3D à portée de dominos" Marques, A.-S.; Chataigner, I; Coeffard, V.; Vincent, G.; Moreau, X. L'Actualité Chimique 2021, 459, 27-30

 

2020

• "Bioinspired Divergent Oxidative Cyclizations of Geissoschizine: Total Synthesis of (–)‐17‐nor‐Excelsinidine, (+)‐16‐epi‐Pleiocarpamine, (+)‐16‐Hydroxymethyl‐Pleiocarpamine and (+)‐Taberdivarine H" Jarret, M.; Tap, A.; Turpin, V.; Denizot, N.; Kouklovsky, C.; Poupon, E.*; Evanno, L.*; Vincent, G.* Eur. J. Org. Chem. 2020, 6340-6351 (front cover).

          "YourJOC Talents" special collection

Dedicated to the Memory of Prof. Robert M. Williams

 

• "Bioinspired Divergent Oxidative Cyclization from Strictosidine and Vincoside Derivatives: Second Generation Total Synthesis of Cymoside and Access to an Original Hexacyclic‐Fused Furo[3,2‐b]indoline" Dou, Y.; J.; Kouklovsky, C.; Vincent, G.* Chem. Eur. J.  2020, 26, 17190-17194. (Hot Paper)

 

• "Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative" Dou, Y.; Kouklovsky, C.; Gandon, V.; Vincent, G.* Angew. Chem. Int. Ed.  2020, 59, 1527-1531.

Highlighted in  Synfact, 2020, 16(4), 0372.

 

• "Dearomatization Reactions of Indoles to Access 3D Indoline Structures" Abou-Hamdan, H.; Kouklovsky, C.; Vincent, G.* Synlett 2020, 31, 1775-1788 (account)

 

• "Electrochemical dihydroxylation and hydroxycyclization of indoles" Wu, J.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Adv. Synth. Catal. 2020, 62, 1712-1719.

 

• "Electrochemical synthesis of 3a-bromofuranoindolines and 3a-bromopyrroloindolines mediated by MgBr₂" Wu, J.; Abou-Hamdan, H.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Chem. Commun. 2020, 56, 1713-1716.

 

2019

• "A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4‐Dienals through an Interrupted iso‐Nazarov Reaction" Marques, A.-S.; Duhail, T.; Marrot, J.; Chataigner, I.*;  C.; Coeffard, V.*; Vincent, G.* Moreau, X.* Angew. Chem. Int. Ed.  2019, 58,  9969-9973.

Communication from CNRS

 

• "Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for Enantioselective Total Synthesis of Mavacuran Alkaloids" Jarret, M.; Turpin, V.; Tap, A.; Gallard, J.F.; Kouklovsky, C.; Poupon, E.*; Vincent, G.* Evanno, L.* Angew. Chem. Int. Ed.  2019, 58, 9861-9865.

Communication from CNRS

Highlighted in  “Organic Chemistry Portal“ web site.

 

• "Synthesis of 3,3-Spirocyclic-2-Phosphono-Indolines via a Dearomative Addition of Phosphonyl Radicals to Indole" Ryzhakov, D.; Jarret, M.; Baltaze, J.-P.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Org. Lett. 2019, 21, 4986-4990.

• "Electrochemical Dearomative 2,3-Difunctionalization of Indoles" Wu, J.; Dou, Y.; Guillot, R.; Kouklovsky, C.; Vincent, G.* J. Am. Chem. Soc. 2019, 141, 2832-2837.

Communication from CNRS

 

• "Dearomatization of 3‐Nitroindoles with Highly γ‐Functionalized Allenoates in Formal (3+2) Cycloadditions" Birbaum, L.; Gillard, L.; Gérard, H.; Oulyadi, H.; Vincent, G.; Moreau, X.; De Paolis, M.*; Chataigner, I.* Chem. Eur. J.. 2019, 25, 13688-13693.

• "Synthèses totales bio-inspirées de substances naturelles - concepts" Poupon, E.; Evanno, L.;  Vincent, G. Les Techniques de l'Ingénieur, 2019, 25, PHA2005 v1.

 

2018

• "Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Total Synthesis of (–)-17-nor-Excelsinidine" Jarret, M.; Tap, A.; Kouklovsky, C.; Poupon, E.; Evanno, L.*; Vincent, G.* Angew. Chem. Int. Ed. 2018, 57, 12294-12298.

Communication from CNRS

Highlighted in  Synfact, 2018, 14(8), 0785.

 

• "Dearomative Diallylation of N-Acyl Indoles Mediated by FeCl₃" Wu, J.; Nandi, R. K.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Org. Lett. 2018, 20, 1845-1848.

 

• "In Situ Generation of Cyclopentadienol Intermediates from 2,4-Dienals. Application to the Synthesis of Spirooxindoles via a Domino Polycyclization" Marques, A.-S.; Marrot, J.; Chataigner, I.; Coeffard, V.*; Vincent, G.*; Moreau, X.* Org. Lett. 2018, 20, 792-795.

        

 

• "N-Iodosuccinimide-Mediated Oxidative Coupling of Indoles and Phenols: A Synthetic Study Toward the Benzofuroindoline Moiety of Bipleiophylline." Denizot, N.; Guillot, R.; Kouklovsky, C. Vincent, G.* Synthesis, 2018, 50, 4823-4828. ("Modern Dearomatization Strategies in Synthesis" special section, invitation from Pr. E. Carreira).

 

• "Divergent Oxidative Couplings between Indoles and 1,2-Dihydroxybenzoic Acid Derivatives for the Biomimetic Synthesis of Voacalgine A and Bipleiophylline" Denizot, N.; Lachkar, D.; Poupon, E.*; Evanno, L.*; Vincent, G.* Synthesis 2018, 50, 4229-4242.

• "Triflic Acid as an Efficient Brønsted Acid Promoter for the Umpolung of N-Ac Indoles in Hydroarylation Reactions" Nandi, R. K.; Perez-Luna, A.; Gori, D.; Beaud, R.; Guillot, R.; Kouklovsky, C.; Gandon, V.*; Vincent. G.* Adv. Synth. Catal. 2018, 360, 161-172.

 

• "Synthèse biomimétique de la bipléiophylline : mimer la nature dans toute sa complexité" Denizot, N.; Lachkar, D.;Kouklovsky, C.; Poupon, E.; Vincent, G.; Evanno, L. L'Actualité Chimique 2018, 429, 37-40.

 

2017

• "Unified biomimetic assembly of voacalgine A and bipleiophylline via divergent oxidative couplings" Lachkar, D.; Denizot, N.; Bernadat, G.; Ahamada, K.; Beniddir, M. A.; Dumontet, V.; Gallard, J.-F.; Guillot, R.; Leblanc, K.; Otogo N'nang, E.; Turpin, V.; Kouklovsky, C.; Poupon, E.*; Evanno, L.*; Vincent. G.* Nat. Chem. 2017, 9, 793-798.

Highlighted in  Synform

Communication from CNRS

Communication from Université Paris-Sud

 

• "Radical-Mediated Dearomatization of Indoles with Sulfinate Reagents for the Synthesis of Fluorinated Spirocyclic Indolines" Ryzhakov, D.; Jarret, M.; Kouklovsky, C.; Vincent. G.* Org. Lett. 2017, 19, 6336-6339.

 

• "Revealing the electrophilicity of N-Ac indoles with FeCl3: a mechanistic study" Beaud, R.; Nandi, R.; Perez-Luna, A.; Guillot, R.; Gori, D.; Kouklovsky, C.; Ghermani, N.*; Gandon, V.*; Vincent, G.* Chem. Commun. 2017, 53, 5834-5837.

 

• "Expedient Approach to α,β-Unsaturated δ-Lactones through a Catalytic Asymmetric [2+2] Cycloaddition" Rousseau, A.; Buchotte, M.; Guillot, R.; Vincent, G.; Kouklovsky, C.*  Eur .J. Org. Chem. 2017, 6804-6810. (Very Important Paper)

 

• "Evaluation of an NIS-Mediated Oxidative Cyclisation of Phenol-Containing N-Acyltryptamine Precursors towards Phalarine: Synthesis of 4′,5′-Dihydrospiro[indole-3,6′-[1,3]oxazine]s" Tomakinian, T.; Abou Hamdan, H.; Denizot, N.; Guillot, R.; Baltaze, J.-P.; Kouklovsky, C.; Vincent, G.* Eur .J. Org. Chem. 2017, 2757-2763.

 

2016

• "Iron-Mediated Domino Interrupted Iso-Nazarov/Dearomative (3 + 2)-Cycloaddition of Electrophilic Indoles" Marques, A.-S.; Coeffard, V.; Chataigner, I.; Vincent, G.*; Moreau, X.* Org. Lett. 2016, 18, 5296-5299.

 

• "Synthesis of Benzofuro[3,2-b]indoline Amines by a Deamination-Interrupted Fischer Indolization and their Unexpected Reactivity Towards Nucleophiles" Tomakinian, T.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Chem. Commun. 2016  52, 5443-5446.

 

• "Intermolecular Dearomative C2-Arylation of N-Ac Indoles Activated by FeCl3." Nandi, R. K.; Ratsch, F.; Beaud, R.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Chem. Commun. 2016  52, 5328-5331.

 

• "Synthesis of 3,3-Spiroindolines via FeCl3-Mediated Cyclization of Aryl- or Alkene-Containing 3-Substituted N–Ac Indoles" Nandi, R.K.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Org. Lett. 2016, 18, 1716-1719.

Highlighted in Synfacts 2016, 12 (6), 0621. 

 

2015

• "Connecting Tyrosine and Tryptophan Units of Diazonamide A and Azonazine by a Diastereodivergent Arylative Dearomatization" Denizot, N.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Chem. Eur. J. 2015, 21, 18953-18956.

 

• "Synthesis of 3-Arylated Indolines from Dearomatization of Indoles" Denizot, N.; Tomakinian, T.; Beaud, R.; Kouklovsky, C.; Vincent, G.* Tetrahedron Lett. 2015, 56, 4413-4429. (Invited Digest article).

 

• "Investigation of the Synthesis of Benzofuroindolines from N-Hydroxyindoles: An O-Arylation/[3,3]-Sigmatropic Rearrangement Sequence" Tomakinian, T.; Kouklovsky, C.; Vincent, G.* Synlett 2015, 1269-1275.

 

• “ The quest of an oxidative coupling of phenols and indoles towards benzofuroindolines: a two stage approach” Beaud, R.; Tomakinian, T.; Denizot, N.; Pouilhès, A.; Kouklovsky, C.; Vincent, G.* Synlett  2015, 432-440 (Special Section for the 2014 Young Investigators Workshop in Organic Chemistry of EUCHEMS).

 

2014

• " Bioinspired Direct Access to Benzofuroindolines by Oxidative [3 + 2] Annulation of Phenols and Indoles " Denizot, N.; Pouilhes, A.; Cucca, M.; Beaud, R.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Org. Lett. 2014, 16, 5752-5755.

 

• " Direct Oxidative Coupling of N-Acetyl Indoles and Phenols for the Synthesis of Benzofuroindolines Related to Phalarine " Tomakinian, T.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Angew. Chem. Int. Ed. 2014, 53, 11881-11885. 

Highlighted in  Synform.

 

• " Regioselective Hydroarylation Reactions of C3 Electrophilic N-Acetyl Indoles activated by FeCl₃. An Entry into 3-(Hetero)Aryl Indolines " Beaud, R.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Chem. Eur. J. 2014, 20, 7492-7500.

 

2013

• " Stereodivergent synthesis of piperidine alkaloids by ring-rearrangement metathesis/reductive lactam alkylation of nitroso Diels-Alder cycloadducts" Vincent, G.*; Karila, D.; Khalil, G.; Sancibrao, P.; Gori, D. Kouklovsky, C.* Chem. Eur. J. 2013, 19, 9358-9365.

 

• "Synthesis of oxaspirannic building blocks by regioselective nitroso Diels-Alder reactions" Sancibrao, P.; Gori, D.; Kouklovsky, C.*; Vincent, G.* Chem. Eur. J. 2013, 19, 5557-5560. 

Highlighted in  “Organic Chemistry Portal“ web site.

 

2012

• " FeCl₃-Mediated Friedel–Crafts Hydroarylation with Electrophilic N-Acetyl Indoles for the Synthesis of Benzofuroindolines " Beaud, R.; Guillot, R.; Kouklovsky, C.; Vincent, G.* Angew. Chem. Int. Ed. 2012, 51, 12546-12550.

 

2011

• " Stereodivergent Synthesis of Substituted N,O-Containing Bicyclic Compounds by Sequential Addition of Nucleophiles to N-Alkoxybicyclolactams " Vincent, G.*; Guillot, R.; Kouklovsky, C.* Angew. Chem. Int. Ed. 2011, 50, 1350 –1353. 

Highlighted in Synfacts 2011, (4), 418. 

 

• " Ring-rearrangement metathesis of Nitroso Diels-Alder cycloadducts " Vincent, G.*; Kouklovsky, C.* Chem. Eur. J. 2011, 17, 2972-2980.

 

2010

• "Synthetic Approaches to Racemic Porantheridine and 8-Epihalosaline via a Nitroso Diels-Alder Cycloaddition/ Ring Rearrangement Metathesis Sequence" Sancibrao, P.; Karila, D.; Kouklovsky, C.*; Vincent, G.* J. Org. Chem. 2010, 75, 4333-4336. 

Highlighted in  “Organic Chemistry Portal“ web site.

 

• "New chiral amino acid-derived α-acyloxynitroso reagents for asymmetric nitroso Diels–Alder reactions" Li, H.; Gori, D.; Kouklovsky, C.*; Vincent, G.* Tetrahedron: Asym. 2010, 21, 1507-15010. Henri Kagan 80th birthday special issue.

 

As undergraduate, PhD, postdoc…

• 13. "Oxidation of bis-sulfinyl carbanions as the pivot of ionic/radical tandem reactions” Vincent, G.;  Cheli, S.; Martinez Mallorquin, R.; Abramovitch, A.; Beauviere, S.; Catherine Gomez, C.; Brebion, F.; Marek, I.;   Malacria, M. Goddard, J.-P.*. Fensterbank, L.* C. R. Chim. (Académie des Sciences) 2016, 19, 403-411. 

 

• 12. “New elements on the behavior of a bisulfinylmethyl radical” Martinez-Mallorquin, R. Vincent, G.; Derat, E.; Goddart, J.-P.*; Fensterbank, L.* Austr. J. Chem. 2013, 66, 346-353.

 

• 11. “New Advance in bis(sulfoxides) chemistry” Beauviere, S.; Brebion, F.; Chelli, S.; Delouvrie, B.; Gomez, C.; Kwasnieski, O.; Martinez Mallorquin, R.; Najera, F.; Vincent, G.; Vitale, M.; Derat, E.; Marek, I. Malacria, M. Goddard, J.-P.; Fensterbank, L.* Phosphorus, Sulfur, and Silicon 2013, 188, 367-376.

 

• 10 “Conjugate Additions to Alkylidene Bis-sulfoxides” Brebion, F.; Vincent, G.; Chelli, S.; Kwasnieski, O.; Najera, F.; Delouvrié, B.; Marek, I.; Derat, E.; Goddard, J.-P.;  Malacria, M.*;  Fensterbank, L.* Chem. Asian J. 2011, 6, 1825-1833.

 

• 9 “Regioselectivity of Pictet-Spengler cyclisation reactions to construct pentacyclic frameworks of the ecteinascidin-saframycin class of tetrahydroisoquinoline antitumor antibiotics.” Vincent, G.; Lane, J. W.; Williams, R. M.* Tetrahedron Lett. 2007, 48, 3719-3722.

 

• 8 “Formation of the C3-C4 unsaturated framework of cribrostatin 4 via DEAD-mediated oxidation of an allylic tertiary amine.” Vincent, G.; Chen, Y.; Lane, J. W.; Williams, R. M.* Heterocycles, 2007, 72, 385-398.

 Prof. Kishi special issue

 

• 7 “Asymmetric total synthesis of (^_)-cribrostatin 4 (renieramycin H).” Vincent, G.; Williams, R. M.* Angew. Chem. Int. Ed. 2007, 46, 1517-1520.

Highlighted in Synfact, 2007, 671.

 

• 6  “Studies toward soraphen A: an aldol-metathesis avenue to the macrocyclic framework.”  Vincent, G.; Mansfield, D.; Vors, J. P.; Ciufolini, M. A.* Org. Lett. 2006, 8, 2791-2794.

 

• 5  “Titanium catalysis in the Ugi reaction of -aminoacids with aromatic aldehydes.”  Godet, T.; Bonvin, Y.; Vincent, G.; Merle, D.; Thozet, A.; Ciufolini, M. A.* Org. Lett. 2004, 6, 3281-3284.

 

• 4 “Copper-promoted/catalyzed C-N and C-O bond Cross-coupling with vinylboronic acid and its utilities.”  Lam, P. Y. S.*; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2003, 44, 4927-4931.

 

• 3 “N-Arylation of a-aminoesters with p-tolylboronic acid promoted by copper(II) acetate.” Lam, P. Y. S.*; Bonne, D.; Vincent, G.; Clark, C. G.; Combs, A. P.  Tetrahedron Lett. 2003, 44, 1691-1694.

 

• 2  “Copper-promoted C-N bond Cross-coupling with phenylstannanes.” Lam, P. Y. S.*; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2002, 43, 3091-3094.

 

• 1  “Copper-catalyzed general C-N and C-O bond cross-coupling with arylboronic acids.” Lam, P. Y. S.*; Vincent, G.; Clark, C. G. ; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418.