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

• chemical synthesis of macrocyclic lactones which are the key structural motifs in some biologically active compounds, 14-methyl-2-phenoxy-1-oxa-2-phosphacyclotetradecane 2-oxide (74) was synthesized as the hapten from phenyl hydrogen (12-hydroxytridecyl)phosphonate (73) via Mitsunobu reaction. The

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

• Bram Ryckaert,
• Ellen Demeyere,
• Frederick Degroote,
• Hilde Janssens and
• Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

• mixtures of the desired and undesired positional alkene isomer could be obtained. We believe an outstanding challenge in the field of chemical synthesis is to find mild and catalytic deprotection chemistries for dithiane-type systems, be they reductive, hydrolytic or oxidative. In particular, a more

Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade

• Qian-Ci Gao,
• Yi-Fei Li,
• Jun Xuan and
• Xiao-Qiang Hu

Beilstein J. Org. Chem. 2023, 19, 100–106, doi:10.3762/bjoc.19.10

• and diverse functionalization of the isocoumarin products highlight the tremendous synthetic potential of this methodology in chemical synthesis and drug discovery. Experimental A 10 mL screw-cap vial was charged with enaminone 1 (0.2 mmol), iodonium ylide 2 (0.6 mmol), [Cp*RhCl2]2 (6.2 mg, 5 mol

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

• chemoselective manner [3]. The development of persistent radicals [4] as synthons in chemical synthesis, coupled with the advancements in generating and manipulating transient radicals [5] as cross-coupling partners in an array of chemical reactions, gives access to a wide variety of “new” retrosynthetic

Synthesis of the biologically important dideuterium-labelled adenosine triphosphate analogue ApppI(d₂)

• Petri A. Turhanen

Beilstein J. Org. Chem. 2022, 18, 1466–1470, doi:10.3762/bjoc.18.153

• Petri A. Turhanen University of Eastern Finland, School of Pharmacy, Biocenter Kuopio, P.O. Box 1627, FIN-70211, Kuopio, Finland 10.3762/bjoc.18.153 Abstract The chemical synthesis of the dideuterium-labelled ATP analogue 1-adenosin-5’-yl-3-(3-methylbut-3-en-1,1-d2-1-ol) triphosphoric acid

Dissecting Mechanochemistry III

• Lars Borchardt and
• José G. Hernández

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

• 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

• activation to advance chemical synthesis on various fronts. Therefore, we hope you enjoy reading the variety of manuscripts in this Thematic Issues as much as we enjoyed editing it, which was only possible thanks to the impeccable assistance by the Editorial Team of the Beilstein-Institut. Lars Borchardt and

Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme

• Jia-Hua Huang,
• Jian-Ming Lv,
• Liang-Yan Xiao,
• Qian Xu,
• Fu-Long Lin,
• Gao-Qian Wang,
• Guo-Dong Chen,
• Sheng-Ying Qin,
• Dan Hu and
• Hao Gao

Beilstein J. Org. Chem. 2022, 18, 1396–1402, doi:10.3762/bjoc.18.144

• , including traditional isolation from nature [5][6][7][8] and chemical synthesis [9], have been made to expand the structural diversity of FC-type diterpenoids for drug development. Along with the development of low-cost sequencing technologies and tractable heterologous expression systems, genome mining has

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase

• Sanaz Ahmadipour,
• Alice J. C. Wahart,
• Jonathan P. Dolan,
• Laura Beswick,
• Chris S. Hawes,
• Robert A. Field and
• Gavin J. Miller

Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142

• Chemical synthesis of 6-chloro-6-deoxy- and 6-amino-6-deoxy-mannose 1-phosphates We first required access to appropriate glycosyl 1-phosphates (as putative substrates for enzymatic pyrophosphorylative coupling) to then access the sugar nucleotide GMD probes of type 8 and 9 (Figure 1c). Accordingly

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• in part due to their usefulness in medicinal chemistry [278] and research to reach even more elaborated amines is warranted. Concerning natural product synthesis, which has been the main source of chemical synthesis challenges in the last century, Paul Wender’s approach consisting in also reaching

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• concentrations of substrate, the different kinetic preferences of PPK1 and PPK2 can be observed. The implications of these results for the application of PPKs in chemical synthesis and as enzymes for ATP regeneration systems are discussed. Keywords: ATP regeneration; biocatalyst; ePC-SAFT; polyp; PPK

• likely is the most pragmatic and straightforward preparation of the enzymes for their use in chemical synthesis. The assay setup used for all PPKs is similar to established ATP regeneration systems with PPK2 enzymes, with a 10:1 excess of polyP (calculated as single phosphates [49]) over the nucleotide

Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides

• Md Azadur Rahman,
• Kana Kuroda,
• Hirofumi Endo,
• Norihiko Sasaki,
• Tomoaki Hamada,
• Hiraku Sakai and
• Toshiki Nokami

Beilstein J. Org. Chem. 2022, 18, 1133–1139, doi:10.3762/bjoc.18.117

• one of a few examples of chemical synthesis of chitin oligosaccharides through polyglycosylation of a glucosamine monosaccharide [6]. Recently, we have reported electrochemical polyglycosylation using a glucosamine derivative as a monomer [7]. This is another example of polyglycosylation of a

Synthesis of odorants in flow and their applications in perfumery

• Merlin Kleoff,
• Paul Kiler and
• Philipp Heretsch

Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76

• Originally, musk was obtained from the gland of the musk deer and used as a powerful base note. Due to the high price of musks of natural origin, the vast majority of them is produced by chemical synthesis. Today, a plethora of synthetic musks with a broad structural and olfactory diversity are available

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• the reduction of the environmental effects of chemical synthesis [22]. The use of ultrasonic irradiation allows for optimal mixing of the reactants and the catalyst by enhancing the homogeneity of the reaction medium. It also decreases the chance of agglomeration of the heterogeneous nanoparticles

Chemical and chemoenzymatic routes to bridged homoarabinofuranosylpyrimidines: Bicyclic AZT analogues

• Sandeep Kumar,
• Jyotirmoy Maity,
• Banty Kumar,
• Sumit Kumar and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2022, 18, 95–101, doi:10.3762/bjoc.18.10

• -homoarabinofuranosyl nucleosides 9a,b. Chemical synthesis of nucleosides 9a,b starting from diacetone ᴅ-glucofuranose. a) Plausible mechanism for the synthesis of (5′R)-3′-azido-3′-deoxy-2′-O,5′-C-bridged-β-ᴅ-homoarabinofuranosyl nucleosides 9a,b from 16a,b and b) intermediates detected on the basis of mass

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

• Thaipparambil Aneeja,
• Cheriya Mukkolakkal Abdulla Afsina,
• Padinjare Veetil Saranya and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 37–52, doi:10.3762/bjoc.18.4

• proposed mechanism for the cyanation step is depicted in Scheme 21. Chemical synthesis usually needs labor-intensive and tiresome procedures. One of the approaches to overcome these challenges is to perform the reactions in flow [44]. The major advantages of this approach include predictable reaction scale

Chemical syntheses and salient features of azulene-containing homo- and copolymers

• Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

• -containing homo- and copolymers, including brief descriptions of their key properties. Keywords: azulene; chemical synthesis; copolymer; non-alternant hydrocarbon; organic electronics; polyazulene; Introduction Azulene (C10H8) is a non-alternant, non-benzenoid, 10 π electron aromatic hydrocarbon containing

• chemical and electrochemical means. Through electrochemical methods, only the five-membered rings can be incorporated onto the polymer backbone, and often the polymers produced are insoluble [17]. On the other hand, chemical synthesis provides an avenue to synthesize soluble polymers where azulene can be

• are needed, and often the synthesis of such building blocks is challenging. This could be the reason why the chemical synthesis of azulene-containing polymers is only sporadically investigated. Hence, this article is intended to provide readers an overview of the developments in the area of chemical

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• and enzymatic methods have been optimized to obtain samples with well-defined substitution patterns and narrow molecular weight distribution. Chemical synthesis has granted access to polysaccharides with full control over the length. Here, we review the progress towards the synthesis of well-defined

• polymerization [18], C) chemical synthesis. The use of enzymes has undeniable advantages because it offers the possibility to use unprotected sugars as substrates and guarantees remarkable control of the regio- and stereoselectivity during glycosylation. Mono- or oligosaccharides bearing a reactive leaving group

• be quite challenging to prepare. Moreover, problems can occur during the removal of the PGs, since partially deprotected compounds can generate insoluble aggregates [24]. Incomplete deprotection and residual PGs can largely affect the properties of the obtained polymer. Chemical synthesis provides

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• several chiral centers, and nowadays, several sesquiterpenes have been isolated from plants of the Illicium genus (77–79, Scheme 28A) [160]. (+)-Pseudoanisatin (80) is one example, and its first chemical synthesis was achieved in 12 steps by Maimone and collaborators in 2016 utilizing a straightforward

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

• Eleni Dimitriou and
• Gavin J. Miller

Beilstein J. Org. Chem. 2021, 17, 1527–1532, doi:10.3762/bjoc.17.110

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• salts has been discovered. Results and Discussion Optimization of reaction conditions and chemical synthesis The base-catalyzed imination of aromatic aldehydes is a valuable method in organic synthesis to synthesize a variety of heterocyclic building blocks [29]. Among all the reported iminoesters

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

• Zhonglie Yang,
• Yutong Liu,
• Kun Cao,
• Xiaobin Zhang,
• Hezhong Jiang and
• Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

• challenges to be solved in response, there is no doubt that the future of green chemical synthesis will surely have a very wide prospect for this strategy. The electron transfer process in EDA complexes. Synthesis of benzo[b]phosphorus oxide 3 initiated by an EDA complex. Mechanism of the synthesis of

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

• Anthony J. Fernandes,
• Armen Panossian,
• Bastien Michelet,
• Agnès Martin-Mingot,
• Frédéric R. Leroux and
• Sébastien Thibaudeau

Beilstein J. Org. Chem. 2021, 17, 343–378, doi:10.3762/bjoc.17.32

• ↔142’ (Scheme 35). Oxygen-stabilized α-(trifluoromethyl)carbenium ions (oxocarbenium ions) have been exploited for chemical synthesis [92][93][94]. Ketone 143a and ketoxime 143b undergo Friedel–Crafts reactions in the presence of Brønsted or Lewis acid to furnish the corresponding CF3-containing

Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

• Dimas J. P. Lima,
• Antonio E. G. Santana,
• Michael A. Birkett and
• Ricardo S. Porto

Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4

• this precursor in (−)-adaline, supporting fatty acid origin for this alkaloid. Reflex bleeding is costly due to energy expended in chemical synthesis and fluid loss. Therefore, it is only deployed when other strategies have failed, and the ladybird is in severe danger [35][36]. A massive discrepancy in

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

• Julia N. Artsemyeva,
• Ekaterina A. Remeeva,
• Tatiana N. Buravskaya,
• Irina D. Konstantinova,
• Roman S. Esipov,
• Anatoly I. Miroshnikov,
• Natalia M. Litvinko and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212

• consisting in the chemical synthesis of N7-methyl derivatives of guanosine (N7Me-Gua) [30][32][33][34][35] and 2'-deoxyguanosine (N7Me-dGua) [31][34][36][37], and the desired Rib-1Pi and dRib-1Pi were obtained in high yields [35][36][37]. The final aim of these studies was the synthesis of biologically

• in cladribine synthesis The dual function of QAE Sephadex A-25 noted above was tested in the enzymatic synthesis of cladribine using dRib-1Pi as a barium salt and bound to the resin. Chemical synthesis of this nucleoside, which has a wide spectrum of pharmacological activities [6][63][64][65], is

Dawn of a new era in industrial photochemistry: the scale-up of micro- and mesostructured photoreactors

• Emine Kayahan,
• Mathias Jacobs,
• Leen Braeken,
• Leen C.J. Thomassen,
• Simon Kuhn,
• Tom van Gerven and
• M. Enis Leblebici

Beilstein J. Org. Chem. 2020, 16, 2484–2504, doi:10.3762/bjoc.16.202

• intrinsic kinetics. This would reduce the reactor size and downstream the processing costs while increasing the safety. The design considerations for microreactors that aim at large-scale chemical synthesis are significantly different from the lab-on-a-chip concept. While gathering intrinsic kinetic data