Institut de Chimie Moléculaire et des Matériaux d'Orsay

Cyrille Kouklovsky

Professeur
Bât. 670, bureau 1411 – MSMT – ICMMO - UMR 8182
Université Paris-Saclay
Bâtiment 670
17-19 Avenue des Sciences
91400 Orsay
FRANCE

+33 1 69 15 73 91
cyrille.kouklovsky@u-psud.fr
https://orcid.org/0000-0001-5399-9469

CV

1986-1989 PhD, Université Paris-XI (Advisor: Y. Langlois)

1991-1994 Post-Doc Imperial College, London and University of Cambridge (Advisor: S.V. Ley)

1995-2003 CNRS Research Fellow, Université de Paris-Sud

2000 HDR Diploma, Université de Paris-Sud

2003- Professor of Organic Chemistry, Université de Paris-Sud

Research Responsabilities

2014- Leader of the MSMT Team

Scientific Responsabilities

2012-2015 Secretary of the Organic Chemistry Division of the French Chemical Society

2015-2018 President of the Organic Chemistry Division of the French Chemical Society

Teaching Responsabilities

2015-2022 Coordinator of the 2nd year Master of Organic Chemistry at Université Paris-Saclay

 

Publications

Natural Product Synthesis: The Endless Quest for Unreachable Perfection. N. Fay, C. Kouklovsky, A. De La Torre, ACS Org. Inorg. Au, 2023, 3, 350-363

Total Synthesis of Lucidumone: Attempted Shortcuts, Dead Ends and Lessons Learnt. G. Huang, A. Laporte, L. Pagès, C. Kouklovsky, A. De La Torre, Synthesis, 2023, 55, A-H

Total Synthesis of Mavacuran Alkaloids via Bioinspired and Non-Bioinspired Strategies. C. Kouklovsky, E. Poupon, L. Evanno, G. Vincent, Synlett, 2023

Retro-[4+2]/Intramolecular Diels–Alder Cascade Allows a Concise Total Synthesis of Lucidumone. G. Huang, C. Kouklovsky, A. De La Torre, Synlett, 2023, 34, 1195-1199

Diversity in the Synthesis of Functionalized Cyclohexene Oxide Derivatives by a Cycloaddition–Fragmentation Sequence from Benzene Oxide. F. Rambaud, R. Guillot, V. Alezra, C. Kouklovsky, J. Org. Chem., 2023, 88, 7152-7161

Using the Noncanonical Metallo-Amino Acid [Cu(II)(2,2′-Bipyridin-5-yl)]-alanine to Study the Structures of Proteins. L. C. Tabares, D. T. Daniel, J. L. Vasquez-Ibar, C. Kouklovsky, V. Alezra, S. Un, J. Phys. Chem. Lett., 2023, 14, 3368-3375

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

Total synthesis of grayanane natural products. N. Fay, R. Blieck, C. Kouklovsky, A. De La Torre, Beilstein J. Org. Chem., 2022, 18, 1707-1719

Diastereo- and Enantioselective Inverse-Electron-Demand Diels–Alder Cycloaddition between 2-Pyrones and Acyclic Enol Ethers. G. Huang, R. Guillot, C. Kouklovsky, B. Maryasin, A. De La Torre, Angew. Chem. Int. Ed., 2022, 61, e202208185

Gram-Scale Enantioselective Synthesis of (+)-Lucidumone. G. Huang, C. Kouklovsky, A. De La Torre, J. Am. Chem. Soc., 2022, 144, 17803-17807

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

Total Synthesis of Ophiorrhine A, G and Ophiorrhiside E Featuring a Bioinspired Intramolecular Diels-Alder Cycloaddition. W. Cao, Y. Dou, C. Kouklovsky, G. Vincent, Angew. Chem. Int. Ed., 2022, 61, e202209135

Highly stereoselective aldol reactions by Memory of Chirality: synthesis of quaternary β-hydroxy α-amino acids. L. Roupnel, R. Guillot, D. Gori, B. Viswambharan, C. Kouklovsky, V. Alezra, Helv. Chim. Act., 2021, 104, e2100127

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

Inverse‐Electron‐Demand Diels–Alder Reactions of 2‐Pyrones: Bridged Lactones and Beyond. G. Huang, C. Kouklovsky, A. De La Torre, Chemistry - A European Journal, 2021, 27, 4760-4788

The chemistry of mavacurane alkaloids: a rich source of bis-indole alkaloids. A. Mauger, M. Jarret, C. Kouklovsky, E. Poupon, L. Evanno, G. Vincent, Nat. Prod. Rep., 2021, 38, 1852-1886

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

The Pivotal Role of N-​O bonds in the Synthesis of Natural Products: A mini-​review. C. Kouklovsky, Vietnam J. Chem., 2020, 58, 20-28

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

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. Y. Dou, C. Kouklovsky, G. Vincent, Chem. Eur. J., 2020, 26, 17190-17194

Dearomatization Reactions of Indoles to Access 3D Indoline Structures. H. Abou-Hamdan, C. Kouklovsky, G. Vincent, Synlett, 2020, 31, 1775-1788

Electrochemical dearomative dihydroxylation and hydroxycyclization of indoles. J. Wu, R. Guillot, C. Kouklovsky, G. Vincent, Adv. Synth. Catal., 2020, 362, 1712-1719

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

Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative. Y. Dou, C. Kouklovsky, V. Gandon, G. Vincent, Angewandte Chemie-International Edition, 2020, 59, 1527-1531

Unexpected dimerization of a tripeptide comprising a β,γ-diamino acid. Y. Wan, J.-P. Baltaze, C. Kouklovsky, E. Miclet, V. Alezra, Journal of Peptide Science, 2019, 25, e3143

Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for Enantioselective Total Synthesis of Mavacuran Alkaloids. M. Jarret, V. Turpin, A. Tap, J.-F. Gallard, C. Kouklovsky, E. Poupon, G. Vincent, L. Evanno, Angewandte Chemie-International Edition, 2019, 58, 9861-9865

Synthesis of 3,3-Spirocyclic 2-Phosphonoindolines via a Dearomative Addition of Phosphonyl Radicals to Indoles. D. Ryzhakov, M. Jarret, J.-P. Baltaze, R. Guillot, C. Kouklovsky, G. Vincent, Org. Lett., 2019, 21, 4986-4990

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

Memory of Chirality in a Flow-Based System: Enantioselective Synthesis of Quaternary α-Amino Acids Using Flow Microreactors. A. Mambrini, D. Gori, C. Kouklovsky, H. Kim, J.-I. Yoshida, V. Alezra, European Journal of Organic Chemistry, 2018, 6754-6757

Oxidative coupling of enolates using memory of chirality: an original enantioselective synthesis of quaternary α-amino acid derivatives. A. Mambrini, D. Gori, R. Guillot, C. Kouklovsky, V. Alezra, Chem. Commun., 2018, 54, 12742-12745

Constrained Cyclic β,γ-Diamino Acids from Glutamic Acid: Synthesis of Both Diastereomers and Unexpected Kinetic Resolution. Y. Wan, N. Auberger, S. Thétiot-Laurent, F. Bouillère, A. Zulauf, J. He, S. Courtiol-Legourd, R. Guillot, C. Kouklovsky, S. Cote Des Combes, C. Pacaud, I. Devillers, V. Alezra, European Journal of Organic Chemistry, 2018, 329-340

N-Iodosuccinimide-Mediated Oxidative Coupling of Indoles and Phenols: A Synthetic Study toward the Benzofuroindoline Moiety of Bipleiophylline. N. Denizot, R. Guillot, C. Kouklovsky, G. Vincent, Synthesis, 2018, 50, 4823-4828

Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Total Synthesis of (‐)‐17‐nor‐Excelsinidine. M. Jarret, A. Tap, C. Kouklovsky, E. Poupon, L. Evanno, G. Vincent, Angewandte Chemie-International Edition, 2018, 57, 12294-12298

Dearomative Diallylation of N-Acylindoles Mediated by FeCl3. J. Wu, R. K. Nandi, R. Guillot, C. Kouklovsky, G. Vincent, Org. Lett., 2018, 20, 1845-1848

Base mediated fragmentation of bicyclic dihydro-3,6-oxazines: transformation of nitroso Diels-Alder cycloadducts. R. Campagne, F. Schäkel, R. Guillot, V. Alezra, C. Kouklovsky, Org. Lett., 2018, 20, 1884-1887

β,γ-Diamino acids as building blocks for new analogues of Gramicidin S: synthesis and biological activity. Y. Wan, A. Stanovych, D. Gori, S. Zirah, C. Kouklovsky, V. Alezra, Eur. J. Med. Chem., 2018, 149, 122-128.

Divergent Oxidative Couplings between Indoles and 2,3-Dihydroxybenzoic Acid Derivatives for the Biomimetic Synthesis of Voacalgine A and Bipleiophylline. N. Denizot, D. Lachkar, C. Kouklovsky, E. Poupon, L. Evanno, G. Vincent, Synthesis, 2018, 50, 4229-4242

Triflic acid as an efficient Brønsted acid promoter for the Umpolung of N-Ac indoles in hydroarylation reactions. R. K. Nandi, A. Perez-Luna, D. Gori, R. Beaud, R. Guillot, C. Kouklovsky, V. Gandon, G. Vincent, Adv. Synth. Catal., 2018, 360, 161–172

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

Expedient Approach to α,β-Unsaturated δ-Lactones via a Catalytic Asymmetric [2+2] Cycloaddition. C. Kouklovsky, A. Rousseau, M. Buchotte, R. Guillot, G. Vincent, Eur. J. Org. Chem., 2017, 6804-6810

Frozen Chirality of Tertiary Aromatic Amides :Access to Enantioenriched Tertiary alpha-Amino Acid or Amino Alcohol without Chiral Reagent. T. T. Mai, B. Viswambharan, D. Gori, R. Guillot, J.-V. Naubron, C. Kouklovsky, V. Alezra, Chem. Eur. J., 2017, 23, 5787-5798

Revealing the Electrophilicity of N-Ac Indoles with FeCl3: a mechanistic study. R. Beaud, R. K. Nandi, A. Perez-Luna, R. Guillot, D. Gori, C. Kouklovsky, N. E. Ghermani, V. Gandon, G. Vincent, Chem. Commun., 2017, 53, 5834 - 5837

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. T. Tomakinian, H. Abou Hamdan, N. Denizot, R. Guillot, J.-P. Baltaze, C. Kouklovsky, G. Vincent, Eur. J. Org. Chem., 2017, 19, 2757–2763

Unified biomimetic assembly of voacalgine A and bipleiophylline via divergent oxidative couplings. D. Lachkar, N. Denizot, G. Bernadat, K. Ahamada, M. A. Beniddir, V. Dumontet, J.-F. Gallard, R. Guillot, K. Leblanc, E. O. N'Nang, V. Turpin, C. Kouklovsky, E. Poupon, L. Evanno, G. Vincent, Nature Chemistry, 2017, 9, 793-798

Efficient synthesis of both diastereomers of β,γ-diamino acids from phenylalanine and tryptophan. N. Auberger, A. Stanovych, S. Thétiot-Laurent, R. Guillot, C. Kouklovsky, S. Cote Des Combes, C. Pacaud, I. Devillers, V. Alezra, Amino Acids, 2016, 48(9), 2237-2242

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

Synthesis of benzofuro[3,2-b]indoline amines via deamination-interrupted Fischer indolization and their unexpected reactivity towards nucleophiles. T. Tomakinian, R. Guillot, C. Kouklovsky, G. Vincent, Chem. Commun., 2016, 52, 5443-5446

Intermolecular dearomative C2-arylation of N-Ac indoles activated by FeCl3. R. K. Nandi, F. Ratsch, R. Beaud, R. Guillot, C. Kouklovsky, G. Vincent, Chem. Commun., 2016, 52, 5328-5331

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

Synthesis of 3-arylated indolines from dearomatization of indoles. N. Denizot, T. Tomakinian, R. Beaud, C. Kouklovsky, G. Vincent, Tetrahedron Lett., 2015, 56, 4413-4429

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

The quest of an oxidative coupling of phenols and indoles towards benzofuroindolines: a two stage approach. R. Beaud, T. Tomakinian, N. Denizot, A. Pouilhès, C. Kouklovsky, G. Vincent, Synlett, 2015, 432-435

Mild Cleavage of N–O Bond of 3,6-Dihydro-1,2-oxazines by Condensation of Aldehydes in Aqueous Media. G. Galvani, R. Lett, C. Kouklovsky, Synlett, 2015, 26, 1340-1344

Substrate Control in Enantioselective and Diastereoselective Aldol Reaction by Memory of Chirality: A Rapid Access to Enantiopure β-Hydroxy Quaternary α-Amino Acids. B. Viswambharan, D. Gori, R. Guillot, C. Kouklovsky, V. Alezra, Org. Lett., 2014, 16, 788-791

Regioselective Hydroarylation Reactions of C3 Electrophilic N-Acetylindoles Activated by FeCl3: An Entry to 3-(Hetero)arylindolines. R. Beaud, R. Guillot, C. Kouklovsky, G. Vincent, Chem. Eur. J., 2014, 20, 7492-7500

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

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

β,γ-Diamino acid: an original building block for hybrid α/γ-peptide synthesis with extra hydrogen bond donating group. A. Stanovych, R. Guillot, C. Kouklovsky, E. Miclet, V. Alezra, Amino Acids, 2014, 46, 2753-2757