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

Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

• Layal Hariss,
• Kamal Bou Hadir,
• Mirvat El-Masri,
• Thierry Roisnel,
• René Grée and
• Ali Hachem

Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208

• , Lebanon Université de Rennes 1, Institut des Sciences Chimiques de Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France 10.3762/bjoc.13.208 Abstract Using an aerobic oxidative coupling, different new imidazo[1,2-a]-N-heterocycles with gem-difluroroalkyl side chains have been

Peptide synthesis: ball-milling, in solution, or on solid support, what is the best strategy?

• Ophélie Maurin,
• Pascal Verdié,
• Gilles Subra,
• Frédéric Lamaty,
• Jean Martinez and
• Thomas-Xavier Métro

Beilstein J. Org. Chem. 2017, 13, 2087–2093, doi:10.3762/bjoc.13.206

• Ophelie Maurin Pascal Verdie Gilles Subra Frederic Lamaty Jean Martinez Thomas-Xavier Metro Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université de Montpellier, ENSCM, Campus Triolet, cc1703, Place Eugène Bataillon, 34095 Montpellier cedex 5, France 10.3762/bjoc.13.206

Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations

• Andrea Porcheddu,
• Evelina Colacino,
• Giancarlo Cravotto,
• Francesco Delogu and
• Lidia De Luca

Beilstein J. Org. Chem. 2017, 13, 2049–2055, doi:10.3762/bjoc.13.202

• Andrea Porcheddu Evelina Colacino Giancarlo Cravotto Francesco Delogu Lidia De Luca Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Cittadella Universitaria, SS 554 bivio per Sestu, 09028 Monserrato (Ca), Italy Institut des Biomolécules Max Mousseron (IBMM

Synthesis of benzannelated sultams by intramolecular Pd-catalyzed arylation of tertiary sulfonamides

• Valentin A. Rassadin,
• Mirko Scholz,
• Anastasiia A. Klochkova,
• Armin de Meijere and
• Victor V. Sokolov

Beilstein J. Org. Chem. 2017, 13, 1932–1939, doi:10.3762/bjoc.13.187

• and analytical data. Acknowledgements V.A.R. gratefully acknowledges the support of the Scientific Council of the President of the Russian Federation (Grant MK-2382.2017.3). M. S. is indebted to the Studienstiftung des Deutschen Volkes for a scholarship. All physicochemical measurements were

Influence of the milling parameters on the nucleophilic substitution reaction of activated β-cyclodextrins

• László Jicsinszky,
• Kata Tuza,
• Giancarlo Cravotto,
• Andrea Porcheddu,
• Francesco Delogu and
• Evelina Colacino

Beilstein J. Org. Chem. 2017, 13, 1893–1899, doi:10.3762/bjoc.13.184

• Montpellier, Institut des Biomolécules Max Mousseron (IBMM) UMR5247 CNRS-UM-ENSCM, Université de Montpellier, cc1703, Place Eugène Bataillon, 34095 Montpellier Cedex 05, France 10.3762/bjoc.13.184 Abstract The present work focuses on the mechanochemical preparation of industrially important β-cyclodextrin

Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation

• Raja Ben Othman,
• Mickaël J. Fer,
• Laurent Le Corre,
• Sandrine Calvet-Vitale and
• Christine Gravier-Pelletier

Beilstein J. Org. Chem. 2017, 13, 1533–1541, doi:10.3762/bjoc.13.153

• -Paris), 45 rue des Saints Pères, 75270 Paris 06, France 10.3762/bjoc.13.153 Abstract The 5’-alkynylation of uridine-derived aldehydes is described. The addition of alkynyl Grignard reagents on the carbonyl group is significantly influenced by the 2’,3’-di-O-protecting groups (R1): O-alkyl groups led to

How and why kinetics, thermodynamics, and chemistry induce the logic of biological evolution

• Addy Pross and
• Robert Pascal

Beilstein J. Org. Chem. 2017, 13, 665–674, doi:10.3762/bjoc.13.66

• Addy Pross Robert Pascal Department of Chemistry, Ben Gurion University of the Negev, Be’er Sheva 84105, Israel NYU Shanghai, 1555 Century Avenue, Pudong New Area, Shanghai, 200122, China, Institut des Biomolécules Max Mousseron, UMR5247 CNRS-University of Montpellier-ENSCM, CC17006, Place E

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

• Loïc Pantaine,
• Vincent Humblot,
• Vincent Coeffard and
• Anne Vallée

Beilstein J. Org. Chem. 2017, 13, 648–658, doi:10.3762/bjoc.13.64

• Loic Pantaine Vincent Humblot Vincent Coeffard Anne Vallee Institut Lavoisier de Versailles, UMR 8180, Université Paris-Saclay, Université de Versailles Saint-Quentin, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France Sorbonne Universités, UPMC Univ. Paris 06, Laboratoire de Réactivité de

• Surface, UMR CNRS 7197, 4 place Jussieu, 75005 Paris, France Université de Nantes, CNRS, CEISAM, UMR 6230, Faculté des Sciences et des Techniques, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France 10.3762/bjoc.13.64 Abstract Aniline-terminated self-assembled monolayers (SAMs) on gold surfaces

• sulfamide. Acknowledgements The authors acknowledge J. Vigneron for help with XPS data collection and the CEFS2 center for the use of XPS instrument. The authors would also like to thank IMPC (Institut des Matériaux de Paris Centre, FR2482) and the C’ Nano projects of the Region Ile-de-France for Omicron

Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

• Sophie Letort,
• Michaël Bosco,
• Benedetta Cornelio,
• Frédérique Brégier,
• Sébastien Daulon,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2017, 13, 417–427, doi:10.3762/bjoc.13.45

• Sophie Letort Michael Bosco Benedetta Cornelio Frederique Bregier Sebastien Daulon Geraldine Gouhier Francois Estour Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France DGA Maîtrise NRBC, Département Evaluation des effets des agents chimiques, 91710 Vert le Petit

Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues

• Bemba Sidi Mohamed,
• Christian Périgaud and
• Christophe Mathé

Beilstein J. Org. Chem. 2017, 13, 251–256, doi:10.3762/bjoc.13.28

• Bemba Sidi Mohamed Christian Perigaud Christophe Mathe Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, Université de Montpellier, CNRS, ENSCM, cc 1705, Site Triolet, Place Eugène Bataillon, 34095 Montpellier cedex 5, France 10.3762/bjoc.13.28 Abstract The racemic synthesis of new

Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• component in the mixture [45]. Furthermore, it was reported that batch heating also resulted in the thermal degradation of choline chloride:D-fructose DES due to the caramelisation of D-fructose [45]. TSE overcame the problems identified by batch heating. The residence time for the continuous extrusion of

• the DES components was determined to be 4–8 minutes on average, producing quantities of ca. 0.4 kg h−1 (value of Reline 200 collected per hour) of DES [44]. The reaction times in the formation of DESs was greatly decreased, and as a result, thermal degradation was avoided in those DESs containing D

• material obtained, which may in turn make them a more accessible media for metal processing or an alternative green solvent for synthesis [44]. Metal-organic frameworks (MOFs) The above examples of cocrystal and DES formation describe systems which involve the formation of eutectic and intermolecular

Poly(ethylene glycol)s as grinding additives in the mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins

• Andrea Mascitti,
• Massimiliano Lupacchini,
• Ruben Guerra,
• Ilya Taydakov,
• Lucia Tonucci,
• Nicola d’Alessandro,
• Frederic Lamaty,
• Jean Martinez and
• Evelina Colacino

Beilstein J. Org. Chem. 2017, 13, 19–25, doi:10.3762/bjoc.13.3

• Montpellier, Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS - UM - ENSCM, Place E. Bataillon, Campus Triolet, 34095 Montpellier CEDEX 5, France P.N. Lebedev Institute of Physics of RAS, Leninskiy pr-t, 53, 119991, Moscow, Russia Moscow Institute of Physics and Technology, Institutskiy per., 9