Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties

• Liliia Moshniaha,
• Marika Żyła-Karwowska,
• Joanna Cybińska,
• Piotr J. Chmielewski,
• Ludovic Favereau and
• Marcin Stępień

Beilstein J. Org. Chem. 2020, 16, 895–903, doi:10.3762/bjoc.16.81

• Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, F-35000 Rennes, France 10.3762/bjoc.16.81 Abstract Boomerang-shaped bipyrroles containing donor–acceptor units were obtained through a tandem palladium-mediated reaction consisting of a cyclization step, involving double C–H bond

Diversity-oriented synthesis of 17-spirosteroids

• Benjamin Laroche,
• Thomas Bouvarel,
• Martin Louis-Sylvestre and
• Bastien Nay

Beilstein J. Org. Chem. 2020, 16, 880–887, doi:10.3762/bjoc.16.79

• Benjamin Laroche Thomas Bouvarel Martin Louis-Sylvestre Bastien Nay Unité Molécules de Communication et Adaptations des Micro-organismes (MCAM), Muséum National d'Histoire Naturelle, CNRS, Paris, France Laboratoire de Synthèse Organique, Ecole Polytechnique, CNRS, ENSTA, Institut Polytechnique de

• spectra. Acknowledgements Dr. Alain Blond and Alexandre Deville are gratefully acknowledged for NMR spectra, and Dr. Sophie Bourcier for HRMS spectra. Funding We thank the CNRS "Fondation pour le développement de la Chimie des Substances Naturelles et ses Applications" for granting a PhD fellowship to BL

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

• Valerian Dragutan,
• Ileana Dragutan,
• Albert Demonceau and
• Lionel Delaude

Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68

• ] accomplished the convergent synthesis of des-epoxy-amphidinolide N (5) in 33 total steps (22 longest linear). To this end, after three generations of synthetic attempts, they succeeded joining the northern and southern fragments of des-epoxy-amphidinolide N, both endowed with a considerable level of structural

• -metal-catalyzed transformations were needed to achieve the total synthesis of des-epoxy-amphidinolide N, including a palladium asymmetric allylic alkylation (Pd-AAA), a Mukaiyama aldol reaction (with Sn), and a Krische allylation (with Ir) [72]. As special feature of this procedure, an Evans aldol

• reaction generated the syn aldol adduct, having the steric configuration imposed in des-epoxy-amphidinolide N. Also, in the last step of their work, Trost et al. managed to install the C14-OH via a finely tuned Rubottom oxidation that finalized the total synthesis of des-epoxy-amphidinolide N. Strikingly

Photoreversible stretching of a BAPTA chelator marshalling Ca²⁺-binding in aqueous media

• Aurélien Ducrot,
• Arnaud Tron,
• Robin Bofinger,
• Ingrid Sanz Beguer,
• Jean-Luc Pozzo and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2019, 15, 2801–2811, doi:10.3762/bjoc.15.273

• Aurelien Ducrot Arnaud Tron Robin Bofinger Ingrid Sanz Beguer Jean-Luc Pozzo Nathan D. McClenaghan Institut des Sciences Moléculaires, CNRS UMR 5255, Univ. Bordeaux, 351 cours de la Libération, 33405 Talence, France 10.3762/bjoc.15.273 Abstract Free calcium ion concentration is known to govern

A photochemical determination of luminescence efficiency of upconverting nanoparticles

• Baptiste Amouroux,
• Clément Roux,
• Jean-Claude Micheau,
• Fabienne Gauffre and
• Christophe Coudret

Beilstein J. Org. Chem. 2019, 15, 2671–2677, doi:10.3762/bjoc.15.260

• Baptiste Amouroux Clement Roux Jean-Claude Micheau Fabienne Gauffre Christophe Coudret Laboratoire des IMRCP, Université de Toulouse, CNRS UMR 5623, Université Toulouse III - Paul Sabatier,118 route de Narbonne, 31062 Toulouse, France Université de Rennes, CNRS, UMR6226, ISCR, F-35000 Rennes

Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis

• Zhen Cao,
• Aline Lacoudre,
• Cybille Rossy and
• Brigitte Bibal

Beilstein J. Org. Chem. 2019, 15, 2465–2472, doi:10.3762/bjoc.15.239

• Zhen Cao Aline Lacoudre Cybille Rossy Brigitte Bibal Université de Bordeaux, Institut des Sciences Moléculaires, UMR CNRS 5255, 351 cours de la libération, 33405 Talence, France 10.3762/bjoc.15.239 Abstract The bis-ortho-thioether 9,10-bis[(o-methylthio)phenyl]anthracene was synthesized as a syn

Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

• Anne-Marie Caminade,
• Artem Zibarov,
• Eduardo Cueto Diaz,
• Aurélien Hameau,
• Maxime Klausen,
• Kathleen Moineau-Chane Ching,
• Jean-Pierre Majoral,
• Jean-Baptiste Verlhac,
• Olivier Mongin and
• Mireille Blanchard-Desce

Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221

• Cedex 4, France LCC-CNRS, Université de Toulouse, CNRS, Toulouse, France Univ. Bordeaux, ISM (CNRS-UMR5255), Bat A12, 351 Cours de la Libération, 33400 Talence, France Univ. Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), UMR 6226, F-35000 Rennes, France 10.3762/bjoc.15.221 Abstract

1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss

• Arnault Heynderickx,
• Sébastien Nénon,
• Olivier Siri,
• Vladimir Lokshin and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2019, 15, 2059–2068, doi:10.3762/bjoc.15.203

• Supporting Information File 110: Experimental and calculated IR spectra of 3, UV–vis absorption spectra of 3 in toluene and its fitting with Pekarian function, NMR spectra. Acknowledgements This work was supported by the Centre National de la Recherche Scientifique, the Ministère de la Recherche et des

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells

• Quentin Huaulmé,
• Cyril Aumaitre,
• Outi Vilhelmiina Kontkanen,
• David Beljonne,
• Alexandra Sutter,
• Gilles Ulrich,
• Renaud Demadrille and
• Nicolas Leclerc

Beilstein J. Org. Chem. 2019, 15, 1758–1768, doi:10.3762/bjoc.15.169

• Quentin Huaulme Cyril Aumaitre Outi Vilhelmiina Kontkanen David Beljonne Alexandra Sutter Gilles Ulrich Renaud Demadrille Nicolas Leclerc CEA, Univ. Grenoble Alpes, CNRS, IRIG, SyMMES, F-38000 Grenoble, France Chimie des Matériaux Nouveaux & Centre d'Innovation et de Recherche en Matériaux

Switchable selectivity in Pd-catalyzed [3 + 2] annulations of γ-oxy-2-cycloalkenones with 3-oxoglutarates: C–C/C–C vs C–C/O–C bond formation

• Yang Liu,
• Julie Oble and
• Giovanni Poli

Beilstein J. Org. Chem. 2019, 15, 1107–1115, doi:10.3762/bjoc.15.107

• Yang Liu Julie Oble Giovanni Poli Sorbonne Université, Faculté des Sciences et Ingénierie, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, 4 place Jussieu, 75005 Paris, France 10.3762/bjoc.15.107 Abstract Two complementary [3 + 2] annulation protocols between 3-oxoglutarates and cyclic γ-oxy

Azologization of serotonin 5-HT₃ receptor antagonists

• Karin Rustler,
• Galyna Maleeva,
• Piotr Bregestovski and
• Burkhard König

Beilstein J. Org. Chem. 2019, 15, 780–788, doi:10.3762/bjoc.15.74

• Karin Rustler Galyna Maleeva Piotr Bregestovski Burkhard Konig Institute of Organic Chemistry, University of Regensburg, 93053 Regensburg, Germany Aix-Marseille University, INSERM, INS, Institut de Neurosciences des Systèmes, 13005 Marseille, France Department of Normal Physiology, Kazan State

• hybrid biomolecule. In this context, various photochromic scaffolds including dithienylethenes, fulgi(mi)des, and azobenzenes are investigated [31][42]. The latter ones were already discovered in 1834 by E. Mitscherlich [43] but it took around another 100 years till G. S. Hartley [44] revealed their

Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes

• Guillaume Ernouf,
• Jean-Louis Brayer,
• Christophe Meyer and
• Janine Cossy

Beilstein J. Org. Chem. 2019, 15, 333–350, doi:10.3762/bjoc.15.29

• , 145 chemin des lilas, 59310 Beuvry-la-Forêt, France 10.3762/bjoc.15.29 Abstract Cyclopropenes constitute useful precursors of other classes of compounds incorporating a three-membered ring. Although the transformation of substituted cyclopropenes into alkylidenecyclopropanes can be accomplished

Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

• Pierre-Antoine Nocquet,
• Aurélie Macé,
• Frédéric Legros,
• Jacques Lebreton,
• Gilles Dujardin,
• Sylvain Collet,
• Arnaud Martel,
• Bertrand Carboni and
• François Carreaux

Beilstein J. Org. Chem. 2018, 14, 2949–2955, doi:10.3762/bjoc.14.274

• Pierre-Antoine Nocquet Aurelie Mace Frederic Legros Jacques Lebreton Gilles Dujardin Sylvain Collet Arnaud Martel Bertrand Carboni Francois Carreaux Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), UMR 6226, 263 avenue du Général Leclerc, Campus de Beaulieu, F-35000 Rennes

• , France Institut des Molécules et Matériaux du Mans, UMR 6283 CNRS-Université du Maine, avenue Olivier Messiaen, 72085 Cedex Le Mans, France Chimie Et Interdisciplinarité: Synthèse, Analyse, Modélisation (CEISAM), UMR 6230 CNRS-Université de Nantes, 2 chemin de la Houssinière, 44322 Cedex Nantes, France

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

• Nadia Bouzayani,
• Jamil Kraїem,
• Sylvain Marque,
• Yakdhane Kacem,
• Abel Carlin-Sinclair,
• Jérôme Marrot and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

• Nadia Bouzayani Jamil Kraїem Sylvain Marque Yakdhane Kacem Abel Carlin-Sinclair Jerome Marrot Bechir Ben Hassine Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène, (UR 11ES56) Université de Monastir, Faculté des Sciences de Monastir, avenue de l’environnement, 5000 Monastir

• , Tunisie. Fax: (+216) 73 500 278; Tel: (+216) 73 Laboratoire de Développement Chimique, Galénique et Pharmacologique des Médicaments, Faculté de Pharmacie de Monastir, Université de Monastir, Rue Avicenne, 5000 Monastir, Tunisie Université de Versailles Saint-Quentin-en-Yvelines, Institut Lavoisier de

• Versailles (ILV), UMR CNRS 8180, 45 avenue des Etats-Unis, 78 035 Versailles Cedex, France Université de Versailles Saint-Quentin-en-Yvelines, Département de chimie, 45 avenue des Etats-Unis, 78 035 Versailles Cedex, France 10.3762/bjoc.14.271 Abstract New chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5

Protein–protein interactions in bacteria: a promising and challenging avenue towards the discovery of new antibiotics

• Laura Carro

Beilstein J. Org. Chem. 2018, 14, 2881–2896, doi:10.3762/bjoc.14.267

• form the binding pocket (Figure 4) [58][59]. Utilizing a virtual screening of two different databases (i.e., the National Cancer Institute [60] and an in-house collection of 32,000 compounds), Wijfells et al. were able to identify a small-molecule mimic of the des-amino-Leu-Phe (dLF) component of the

Natural and redesigned wasp venom peptides with selective antitumoral activity

• Marcelo D. T. Torres,
• Gislaine P. Andrade,
• Roseli H. Sato,
• Cibele N. Pedron,
• Tania M. Manieri,
• Giselle Cerchiaro,
• Anderson O. Ribeiro,
• Cesar de la Fuente-Nunez and
• Vani X. Oliveira Jr.

Beilstein J. Org. Chem. 2018, 14, 1693–1703, doi:10.3762/bjoc.14.144

• ., Dec-NH2, [Pro]4-Dec-NH2, [Arg]1-Dec-NH2, [Phe]2-Dec-NH2 and [Phe]6-Des[Thr]11-Dec-NH2. The analogs presented similar antitumor activity in growth inhibition assays with MCF-7 breast cancer cells. Dec-NH2, Trp- and Phe-substituted analogs were described as the most hemolytic peptides of their family

• and the other derivatives evaluated (Table 1) and presented higher antimicrobial activity when compared to the other analogs that also exhibited anticancer activity, such as [Pro]4-Dec-NH2 and [Phe]6-Des[Thr]11-Dec-NH2 (Figure 2). We also observed noticeable differences among the Phe-substituted

• peptides. For instance, [Phe]2-Dec-NH2 and [Phe]6-Des[Thr]11-Dec-NH2 inhibited cell viability the most, at 50 μmol L−1 after 2 h (Figure 2). On the other hand, [Phe]6-Dec-NH2 did not show significant inhibition after 2 h and [Phe]9-[Phe]10-Dec-NH2 did only show significant inhibition after 24 h (Figure 2

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

• Gwendal Grelier,
• Benjamin Darses and
• Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

• Gwendal Grelier Benjamin Darses Philippe Dauban Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France 10.3762/bjoc.14.128 Abstract Most of the polyvalent organoiodine compounds derive from

• . Acknowledgements We wish to thank the French National Research Agency (program n° ANR-11-IDEX-0003-02, CHARMMMAT ANR-11-LABX-0039), the Ministère de l’Enseignement Supérieur et de la Recherche (fellowship to G. G.), and the Institut de Chimie des Substances Naturelles for their support.

Steric “attraction”: not by dispersion alone

• Ganna Gryn’ova and
• Clémence Corminboeuf

Beilstein J. Org. Chem. 2018, 14, 1482–1490, doi:10.3762/bjoc.14.125

• Ganna Gryn'ova Clemence Corminboeuf Institut des Sciences et Ingénierie Chimiques, École polytechnique fédérale de Lausanne, CH-1015 Lausanne, Switzerland 10.3762/bjoc.14.125 Abstract Non-covalent interactions between neutral, sterically hindered organic molecules generally involve a strong

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

• Cristina Cebrián and
• Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

• Cristina Cebrian Matteo Mauro Université de Lorraine, CNRS, L2CM, F-57000 Metz, France Université de Strasbourg, CNRS – Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), UMR 7504, 23 rue du Loess, F-67000 Strasbourg, France 10.3762/bjoc.14.124 Abstract Phosphorescent

Iodine(III)-mediated halogenations of acyclic monoterpenoids

• Laure Peilleron,
• Tatyana D. Grayfer,
• Joëlle Dubois,
• Robert H. Dodd and
• Kevin Cariou

Beilstein J. Org. Chem. 2018, 14, 1103–1111, doi:10.3762/bjoc.14.96

• Laure Peilleron Tatyana D. Grayfer Joelle Dubois Robert H. Dodd Kevin Cariou Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France 10.3762/bjoc.14.96 Abstract Five different

Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins

• Robby Vroemans,
• Fante Bamba,
• Jonas Winters,
• Joice Thomas,
• Jeroen Jacobs,
• Luc Van Meervelt,
• Jubi John and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 626–633, doi:10.3762/bjoc.14.49

• Robby Vroemans Fante Bamba Jonas Winters Joice Thomas Jeroen Jacobs Luc Van Meervelt Jubi John Wim Dehaen Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium Laboratoire de Chimie Organique Structurale, UFR Sciences des Structures de la

Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs)

• Thanh-Tuân Bui,
• Fabrice Goubard,
• Malika Ibrahim-Ouali,
• Didier Gigmes and
• Frédéric Dumur

Beilstein J. Org. Chem. 2018, 14, 282–308, doi:10.3762/bjoc.14.18

• Thanh-Tuan Bui Fabrice Goubard Malika Ibrahim-Ouali Didier Gigmes Frederic Dumur Laboratoire de Physicochimie des Polymères et des Interfaces (LPPI), Université de Cergy-Pontoise, 5 mail Gay Lussac, Neuville sur Oise, 95031 Cergy-Pontoise Cedex, France Aix Marseille Univ, CNRS, Centrale Marseille

Reactivity of bromoselenophenes in palladium-catalyzed direct arylations

• Aymen Skhiri,
• Ridha Ben Salem,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2017, 13, 2862–2868, doi:10.3762/bjoc.13.278

• Aymen Skhiri Ridha Ben Salem Jean-Francois Soule Henri Doucet Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, "Organométalliques: Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France Laboratoire de Laboratoire de Chimie Organique LR 17ES08, Université

• de Sfax, Faculté des Sciences de Sfax, Route de la Soukra km 4, 3038 Sfax, Tunisia 10.3762/bjoc.13.278 Abstract The reactivity of 2-bromo- and 2,5-dibromoselenophenes in Pd-catalyzed direct heteroarylation was investigated. From 2-bromoselenophene, only the most reactive heteroarenes could be

The use of 4,4,4-trifluorothreonine to stabilize extended peptide structures and mimic β-strands

• Yaochun Xu,
• Isabelle Correia,
• Tap Ha-Duong,
• Nadjib Kihal,
• Jean-Louis Soulier,
• Julia Kaffy,
• Benoît Crousse,
• Olivier Lequin and
• Sandrine Ongeri

Beilstein J. Org. Chem. 2017, 13, 2842–2853, doi:10.3762/bjoc.13.276

• Sorbonne Universités, UPMC Univ Paris 06, Ecole Normale Supérieure, PSL Research University, CNRS, Laboratoire des Biomolécules, 4 place Jussieu, 75252 Paris Cedex 05, France 10.3762/bjoc.13.276 Abstract Pentapeptides having the sequence R-HN-Ala-Val-X-Val-Leu-OMe, where the central residue X is L-serine

A mechanochemical approach to access the proline–proline diketopiperazine framework

• Nicolas Pétry,
• Hafid Benakki,
• Eric Clot,
• Pascal Retailleau,
• Farhate Guenoun,
• Fatima Asserar,
• Chakib Sekkat,
• Thomas-Xavier Métro,
• Jean Martinez and
• Frédéric Lamaty

Beilstein J. Org. Chem. 2017, 13, 2169–2178, doi:10.3762/bjoc.13.217

• Nicolas Petry Hafid Benakki Eric Clot Pascal Retailleau Farhate Guenoun Fatima Asserar Chakib Sekkat Thomas-Xavier Metro Jean Martinez Frederic Lamaty Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université de Montpellier, ENSCM, Campus Triolet, Place Eugène Bataillon, 34095

• , France Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France 10.3762/bjoc.13.217 Abstract Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution