Bromination of endo-7-norbornene derivatives revisited: failure of a computational NMR method in elucidating the configuration of an organic structure

• Demet Demirci Gültekin,
• Arif Daştan,
• Yavuz Taşkesenligil,
• Cavit Kazaz,
• Yunus Zorlu and
• Metin Balci

Beilstein J. Org. Chem. 2023, 19, 764–770, doi:10.3762/bjoc.19.56

• may need to re-examine his/her computational approach and try to use it rather in a supportive role in organic chemistry. Structure 6 (our assignment) and structure 7 revised by Novitskiy and Kutateladze. W or M orientaition in norbornane and the corresponding coupling constants. The determined

Synthesis of medium and large phostams, phostones, and phostines

• Jiaxi Xu

Beilstein J. Org. Chem. 2023, 19, 687–699, doi:10.3762/bjoc.19.50

• Jiaxi Xu State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People’s Republic of China College of Sciences, Henan Agricultural University, Zhengzhou 450002, P. R. China 10.3762

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

• Péter Kisszékelyi and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

• Peter Kisszekelyi Radovan Sebesta Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia 10.3762/bjoc.19.44 Abstract Metal enolates are useful intermediates and building blocks indispensable in many

Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

• Josipa Matić,
• Tana Tandarić,
• Marijana Radić Stojković,
• Filip Šupljika,
• Zrinka Karačić,
• Ana Tomašić Paić,
• Lucija Horvat,
• Robert Vianello and
• Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

• Josipa Matic Tana Tandaric Marijana Radic Stojkovic Filip Supljika Zrinka Karacic Ana Tomasic Paic Lucija Horvat Robert Vianello Lidija-Marija Tumir Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta

• 54, 10000 Zagreb, Croatia Laboratory for the Computational Design and Synthesis of Functional Materials, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia Laboratory for Physical Chemistry and Corrosion, Department of Chemistry and

• Biochemistry, Faculty of Food Technology and Biotechnology, University of Zagreb, Croatia Laboratory for Protein Biochemistry and Molecular Modelling, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia Laboratory for Molecular Plant Biology and

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

• Austin Pounder,
• Eric Neufeld,
• Peter Myler and
• William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

• branch of organic chemistry dedicated to the synthesis of highly functionalized products through sequential transformations in a single reaction. Classically, a domino reaction has been defined by Tietze as a reaction involving two or more bond-forming transformations that take place under the same

Total synthesis: an enabling science

• Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 474–476, doi:10.3762/bjoc.19.36

• synthetic methodology developments and to natural product isolation or biosynthesis. Thus, thematic issues dealing with total synthesis in the Beilstein Journal of Organic Chemistry have naturally been published in these fields, such as "Transition-metal and organocatalysis in natural product synthesis

• syntheses ever published in the Beilstein Journal of Organic Chemistry, such as those of frog indolizidine alkaloids [5][6]. However, no thematic issue specifically related to total synthesis has been published before, and we thought it would be time to fill this gap. Although innovative developments are

• harvesting increasingly complex synthetic strategies for industrial processes. Although it can be useful in operating routine processes, AI will not replace human creativity [17]. In terms of discoveries in organic chemistry, total synthesis is a fruitful feed, and serendipity has well been exploited. Even

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

• János Máté Orosz,
• Dóra Ujj,
• Petr Kasal,
• Gábor Benkovics and
• Erika Bálint

Beilstein J. Org. Chem. 2023, 19, 294–302, doi:10.3762/bjoc.19.25

• Janos Mate Orosz Dora Ujj Petr Kasal Gabor Benkovics Erika Balint Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary Department of Organic Chemistry, Faculty

Friedel–Crafts acylation of benzene derivatives in tunable aryl alkyl ionic liquids (TAAILs)

• Swantje Lerch,
• Stefan Fritsch and
• Thomas Strassner

Beilstein J. Org. Chem. 2023, 19, 212–216, doi:10.3762/bjoc.19.20

• acylation; homogeneous catalysis; ionic liquids; iron catalysis; TAAILs; Introduction The Friedel–Crafts acylation is one of the oldest metal-catalyzed reactions in organic chemistry [1] and allows for the synthesis of a broad range of diverse compounds [2][3][4][5]. Starting from electron-rich aromatic

An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies

• Tharun K. Kotammagari,
• Sweta Misra,
• Sayantan Paul,
• Sunita Kunte,
• Rajesh G. Gonnade,
• Manas K. Santra and
• Asish K. Bhattacharya

Beilstein J. Org. Chem. 2023, 19, 204–211, doi:10.3762/bjoc.19.19

• Tharun K. Kotammagari Sweta Misra Sayantan Paul Sunita Kunte Rajesh G. Gonnade Manas K. Santra Asish K. Bhattacharya Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India Academy of Scientific and Innovative Research (AcSIR), CSIR-HRDC Campus

Germacrene B – a central intermediate in sesquiterpene biosynthesis

• Houchao Xu and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

• Houchao Xu Jeroen S. Dickschat Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany 10.3762/bjoc.19.18 Abstract Germacranes are important intermediates in the biosynthesis of eudesmane and guaiane sesquiterpenes. After their

Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

• Angelique Ladwig,
• Markus Kroll and
• Stefan Schulz

Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16

• Angelique Ladwig Markus Kroll Stefan Schulz Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany 10.3762/bjoc.19.16 Abstract Hyperolid reed frogs are one of the few families of Anurans known to possess glands that emit volatile compounds

Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

• Eric Gayon,
• Guillaume Lefèvre,
• Olivier Guerret,
• Adrien Tintar and
• Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

• exogenous N- or P-based ligands, highlighting the efficiency of iron as a credible alternative to noble metal catalysis in cross-coupling chemistry [13]. Cahiez’ pioneering work highlighted the potential of iron catalysis in organic chemistry and generated a new interest for the study of iron-catalyzed

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

• Christian Schumacher,
• Jas S. Ward,
• Kari Rissanen,
• Carsten Bolm and
• Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

• Christian Schumacher Jas S. Ward Kari Rissanen Carsten Bolm Mohamed Ramadan El Sayed Aly Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany University of Jyvaskyla, Department of Chemistry, P.O. Box 35, 40014 Jyväskylä, Finland Chemistry Department, Faculty

Organophosphorus chemistry: from model to application

• György Keglevich

Beilstein J. Org. Chem. 2023, 19, 89–90, doi:10.3762/bjoc.19.8

• Gyorgy Keglevich Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary 10.3762/bjoc.19.8 Keywords: organophosphorus chemistry; The thematic issue “Organophosphorus chemistry: from model to application” shows a number of “hot

NaI/PPh₃-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

• Dan Liu,
• Yue Zhao and
• Frederic W. Patureau

Beilstein J. Org. Chem. 2023, 19, 57–65, doi:10.3762/bjoc.19.5

• Dan Liu Yue Zhao Frederic W. Patureau Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany 10.3762/bjoc.19.5 Abstract A practical NaI/PPh3-catalyzed decarboxylative radical cascade cyclization of N-arylacrylamides with redox-active esters is described, which

Modern flow chemistry – prospect and advantage

• Philipp Heretsch

Beilstein J. Org. Chem. 2023, 19, 33–35, doi:10.3762/bjoc.19.3

• Philipp Heretsch Institute of Organic Chemistry, Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany 10.3762/bjoc.19.3 Keywords: flow chemistry; method development; reactor design; Organic chemistry has shaped modern society by fulfilling the basic needs for pharmaceuticals

• reservations for continuous flow in academia [13]. As guest editor of this thematic issue, I would like to express my gratitude to all authors for their excellent contributions. I thank the referees for providing their expertise and time and the whole team at the Beilstein Journal of Organic Chemistry for

Combining the best of both worlds: radical-based divergent total synthesis

• Kyriaki Gennaiou,
• Antonios Kelesidis,
• Maria Kourgiantaki and
• Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

• Kyriaki Gennaiou Antonios Kelesidis Maria Kourgiantaki Alexandros L. Zografos Aristotle University of Thessaloniki, Department of Chemistry, Laboratory of Organic Chemistry, Thessaloniki, 54124, Greece 10.3762/bjoc.19.1 Abstract A mature science, combining the art of the total synthesis of

• complex natural structures and the practicality of delivering highly diverged lead compounds for biological screening, is the constant aim of the organic chemistry community. Delivering natural lead compounds became easier during the last two decades, with the evolution of green chemistry and the concepts

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

• Elena R. Lopat’eva,
• Igor B. Krylov,
• Dmitry A. Lapshin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

• Elena R. Lopat'eva Igor B. Krylov Dmitry A. Lapshin Alexander O. Terent'ev N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, 119991, Russia 10.3762/bjoc.18.179 Abstract Organocatalysis is widely recognized as a key synthetic methodology in

• organic chemistry. It allows chemists to avoid the use of precious and (or) toxic metals by taking advantage of the catalytic activity of small and synthetically available molecules. Today, the term organocatalysis is mainly associated with redox-neutral asymmetric catalysis of C–C bond-forming processes

• stoichiometric oxidants. The development of organic chemistry is strongly affected by rising “green” demands to synthetic methodologies, including reduction of waste formation, low trace-metal content in drug compounds, high energy-efficiency and selectivity of processes. In the last decade researchers proposed

A new route for the synthesis of 1-deazaguanine and 1-deazahypoxanthine

• Raphael Bereiter,
• Marco Oberlechner and
• Ronald Micura

Beilstein J. Org. Chem. 2022, 18, 1617–1624, doi:10.3762/bjoc.18.172

• Raphael Bereiter Marco Oberlechner Ronald Micura Institute of Organic Chemistry, Center for Molecular Biosciences, Innsbruck (CMBI), Innrain 80-82, 6020 Innsbruck, Austria 10.3762/bjoc.18.172 Abstract Imidazopyridines and pyrrolopyrimidines are an important class of compounds in medicinal

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

• Konstantin Lebedinskiy,
• Volodymyr Lobaz and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

• Konstantin Lebedinskiy Volodymyr Lobaz Jindrich Jindrich Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Prague, Czech Republic Institute of Macromolecular Chemistry, Department of Supramolecular Systems and Self-Assembling Processes, Heyrovského nám. 2

Simple synthesis of multi-halogenated alkenes from 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane)

• Yukiko Karuo,
• Atsushi Tarui,
• Kazuyuki Sato,
• Kentaro Kawai and
• Masaaki Omote

Beilstein J. Org. Chem. 2022, 18, 1567–1574, doi:10.3762/bjoc.18.167

• presence of KOH. In this reaction, halothane plays a key role in the construction of highly halogenated and structurally intriguing products. The tri-halogenated alkenyl ether has potential applications in organic chemistry, e.g., in Suzuki–Miyaura or Sonogashira cross-coupling reactions. Further

A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1H-pyrrole-2,3-diones with diazooxindoles

• Pavel A. Topanov,
• Anna A. Maslivets,
• Maksim V. Dmitriev,
• Irina V. Mashevskaya,
• Yurii V. Shklyaev and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2022, 18, 1532–1538, doi:10.3762/bjoc.18.162

• Pavel A. Topanov Anna A. Maslivets Maksim V. Dmitriev Irina V. Mashevskaya Yurii V. Shklyaev Andrey N. Maslivets Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, Perm 614013, Russian Federation Department of Organic Chemistry, Faculty of Chemistry, Perm State University

Molecular and macromolecular electrochemistry: synthesis, mechanism, and redox properties

• Shinsuke Inagi and
• Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 1505–1506, doi:10.3762/bjoc.18.158

• /bjoc.18.158 Keywords: electron transfer; electrosynthesis; organic electrochemistry; redox-active materials; Electrochemistry is now a powerful tool in organic chemistry not only for analyzing the electron transfer behavior of organic molecules and macromolecules, but also for driving organic

Dissecting Mechanochemistry III

• Lars Borchardt and
• José G. Hernández

Beilstein J. Org. Chem. 2022, 18, 1454–1456, doi:10.3762/bjoc.18.150

• , Colombia 10.3762/bjoc.18.150 In the past ten years, the use of mechanochemical techniques (e.g., grinding, milling, extrusion, pulsed ultrasonication, resonant acoustic mixing, etc.) have widespread in the field of organic chemistry, enabling the development of new and more sustainable protocols for

• chemical synthesis [1][2]. Within this period, the Beilstein Journal of Organic Chemistry has organized two Thematic Issues (i.e., Mechanochemistry and Mechanochemistry II) to facilitate the open dissemination of the best research in the field of synthetic organic mechanochemistry. The great success of

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

• Artem N. Semakin,
• Ivan S. Golovanov,
• Yulia V. Nelyubina and
• Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

• Artem N. Semakin Ivan S. Golovanov Yulia V. Nelyubina Alexey Yu. Sukhorukov Laboratory of organic and metal-organic nitrogen-oxygen systems, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, 119991, Russian Federation Center for molecular

• 2190361, 2190362, 2190363, 2182991, 2182992, 2182993, 2182994, 2182995, 2183048. Acknowledgements The authors thank Dr. M. E. Minyaev, E. I. Tuzharov, and D. I. Nasyrova from the Department of Structural Studies of N. D. Zelinsky Institute of Organic Chemistry for determination of crystal structures for