A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA

• Ekaterina A. Bryushkova,
• Erik R. Gandalipov and
• Julia V. Nuzhina

Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100

• types of compounds. It is most promising to develop simple and effective biosensors for the use in situations where traditional methods are not available due to their complexity and laboriousness. In this project, a novel smart deoxyribozyme-based fluorescent sensor for the detection of androgen

A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes

• Dragana Vuk,
• Irena Škorić,
• Valentina Milašinović,
• Krešimir Molčanov and
• Željko Marinić

Beilstein J. Org. Chem. 2020, 16, 1092–1099, doi:10.3762/bjoc.16.96

• numerous biologically active natural compounds (Figure 1) [4][5][6][7], their strenuous isolation procedures from plants, as well as their complicated multistage synthesis due to the complexity of their structure, encouraged us to develop a simple one-step synthetic procedure based on a photochemical

Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations

• Laura Sršan and
• Thomas Ziegler

Beilstein J. Org. Chem. 2020, 16, 888–894, doi:10.3762/bjoc.16.80

• complexity of the aforementioned macromolecules caused by PTM still constitutes a technical challenge. They can only be applied to small amounts of pure material, which is insufficient for extended biological investigations [4][6]. Hitherto, a variety of glycopeptides are used for medicinal applications, for

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

• their characteristic 3D geometry [68]. In particular, with 17-spirosteroids [69][70][71][72][73][74][75][76], the three dimensional complexity of the steroid CD-ring system is expected to be substantially affected. Results and Discussion The first goal of this work aimed at synthesizing spirocyclic

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

• complexity, by essentially using a Ru-catalyzed alkene–alkyne (Ru-AA) coupling reaction and a macrolactonization step (Scheme 8). In this carefully designed total synthesis, after applying a Marshall coupling reaction aimed at installing a propargyl group into the initial acetylene component, an enyne

• other memory impairments, namely (−)-galanthamine (13), has attracted great interest for its structural complexity and specific bioactivity. The total synthesis of compound 13, described by Brown et al. [81], involved an enyne ring-closing metathesis and a Heck cross-coupling as the key reactions for

• , hydroxylation, etc. This point of view has allowed to master a concise access to the target products which require exceptional chemical and stereochemical complexity. The excellence of the Grubbs- and Schrock-type metathesis catalysts as selective and proficient promoters of enyne metathesis was emphasized. The

Recent advances in Cu-catalyzed C(sp³)–Si and C(sp³)–B bond formation

• Balaram S. Takale,
• Ruchita R. Thakore,
• Elham Etemadi-Davan and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

• alcohol due to decomposition. Nonetheless, several products could be transformed into molecules of greater complexity. For example, cyclopropanation could be achieved to give 269. Additionally, TBS protection of 268 followed by ring closing metathesis (RCM) led to the interesting 6-membered silacycle 270

Synthesis of organic liquid crystals containing selectively fluorinated cyclopropanes

• Zeguo Fang,
• Nawaf Al-Maharik,
• Peer Kirsch,
• Matthias Bremer,
• Alexandra M. Z. Slawin and
• David O’Hagan

Beilstein J. Org. Chem. 2020, 16, 674–680, doi:10.3762/bjoc.16.65

• ], but the complexity of their synthesis has limited their development as practical materials. As a consequence, it continues to be a research objective to introduce polar substituents in a manner that can influence the nature of the dielectric anisotropy of the resultant material. In this context we

Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

• Jan Geldsetzer and
• Markus Kalesse

Beilstein J. Org. Chem. 2020, 16, 670–673, doi:10.3762/bjoc.16.64

• investigations on the construction of the segments 3 and 4 as well as our results on the cross coupling between both fragments. Our retrosynthetic approach (Figure 1) divides chondrochloren A (1) into three fragments of similar complexity: amide 2, (Z)-bromide 4 and amide 3. For the coupling of amide 3 and (Z

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

• Ming-Xi Bi,
• Shuai Liu,
• Yangen Huang,
• Xiu-Hua Xu and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2020, 16, 657–662, doi:10.3762/bjoc.16.62

• construction of compounds with structural diversity and complexity. In 2014, Wang reported the first radical cascade trifluoromethylthiolation and cyclization of activated alkenes (Scheme 1a) [23]. Afterward, Nevado [24], Hopkinson and Glorius [25], Dagousset and Magnier [26], as well as Fu [27] applied this

Opening up connectivity between documents, structures and bioactivity

• Christopher Southan

Beilstein J. Org. Chem. 2020, 16, 596–606, doi:10.3762/bjoc.16.54

• seems that way). The following is a selection: 1.) PubChem presents users with the complexity of parallel systems of D-C connectivity [28]. For medical subject headings (MeSH) the publication links are biased towards common name matches in many papers (e.g., the MeSH category for chemicals and drugs

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

• Bernd Strehmel,
• Christian Schmitz,
• Ceren Kütahya,
• Yulian Pang,
• Anke Drewitz and
• Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

• Delphine Pichon,
• Jennifer Morvan,
• Christophe Crévisy and
• Marc Mauduit

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

• accomplished in this stimulating field. Keywords: acylimidazole; N-acyloxazolidinone; N-acylpyrrole; N-acylpyrrolidinone; aldehyde; amide; copper catalysis; electron-deficient alkenes; enantioselective conjugate addition; Michael acceptor; thioester; Introduction Generating high molecular complexity and

Combination of multicomponent KA² and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones

• Riccardo Innocenti,
• Elena Lenci,
• Gloria Menchi and
• Andrea Trabocchi

Beilstein J. Org. Chem. 2020, 16, 200–211, doi:10.3762/bjoc.16.23

• generate the maximum diversity and complexity from simple starting materials applying divergent synthetic strategies, such as the use of complexity-generating reactions and the build/couple/pair approach [17][18]. The application of multicomponent approaches has proven to be very useful as starting points

• , ring complexity) into single dimensional numerical values (principal components), to simplify the comparison with different sets of compounds. ChemGPS-NP [62][63][64] was chosen for the PCA analysis, providing a comprehensive exploration of the chemical space in terms of global mapping onto a

• 3–39 possess lower tendency to stay in the rod side of the triangle, as compared to BB drugs, suggesting for these compounds a higher shape complexity, as due to the presence of quaternary carbon atoms introduced by the KA2 coupling reaction. The intramolecular Pauson–Khand cyclization proved to be

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

• Alexander Sailer,
• Franziska Ermer,
• Yvonne Kraus,
• Rebekkah Bingham,
• Ferdinand H. Lutter,
• Julia Ahlfeld and
• Oliver Thorn-Seshold

Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

• development beyond classical small molecule inhibitors; since the spatiotemporal complexity inherent to the diversity of tubulin-dependent cellular processes may finally yield to studies that can leverage high-spatiotemporal-specificity optical control to deliver cell-specific, time-reversible modulation of

Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

• Andreas H. Heindl and
• Hermann A. Wegner

Beilstein J. Org. Chem. 2020, 16, 22–31, doi:10.3762/bjoc.16.4

• allow to drastically increase the information storage capacity and complexity of smart materials. In this context, unsymmetrical 1,3,5-tris(arylazo)benzenes – ‘starazos’ – which merge three photoswitches on one benzene ring, were successfully prepared. Two different synthetic strategies, one based on

Terpenes

• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2019, 15, 2966–2967, doi:10.3762/bjoc.15.292

• products. Their remarkable structural complexity and diversity is a result of a unique biosynthetic pathway invented by nature that starts with the formation of only a few acyclic precursors termed oligoprenyl diphosphates. These precursors containing multiple olefinic double bonds can be ionised to

Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis

• David C. B. Siebert,
• Roman Sommer,
• Domen Pogorevc,
• Michael Hoffmann,
• Silke C. Wenzel,
• Rolf Müller and
• Alexander Titz

Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286

• Saarbrücken, Germany 10.3762/bjoc.15.286 Abstract The argyrins are secondary metabolites from myxobacteria with antibiotic activity against Pseudomonas aeruginosa. Studying their structure–activity relationship is hampered by the complexity of the chemical total synthesis. Mutasynthesis is a promising

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

• Eric J. N. Helfrich,
• Geng-Min Lin,
• Christopher A. Voigt and
• Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

• that further increase the structural complexity of terpenoids by adding various functional groups. The size of bacterial terpene BGCs can vary significantly, which can be largely attributed to the presence or absence of tailoring genes. Some BGCs can be as large as modular thiotemplate BGCs (e.g

Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea

• Aleksandr I. Kobelev,
• Nikita A. Tretyakov,
• Ekaterina E. Stepanova,
• Maksim V. Dmitriev,
• Michael Rubin and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2019, 15, 2864–2871, doi:10.3762/bjoc.15.280

• heterocycles are relatively new and insufficiently investigated structures in medicinal chemistry [17][18]. The introduction of spiro-fused cyclic moieties in small molecules increases the degree of their structural (shape) complexity, which may lead to the reduced binding promiscuity and improved clinical

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

• Lorenzo Sansalone,
• Jun Zhao,
• Matthew T. Richers and
• Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

• )AChR. The structural difference between the native acetylcholine and nicotine are striking, and their diversity reflects the complexity of structure–activity relationships of ligands for nicotinic acetylcholine receptors. For example, the drug homocholine phenyl ether (HoChPE) is an agonist of the

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

• Gerardo M. Ojeda,
• Prabhat Ranjan,
• Pavel Fedoseev,
• Lisandra Amable,
• Upendra K. Sharma,
• Daniel G. Rivera and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

• complexity. In addition, the hybrid nature of the final compounds makes them attractive for possible medicinal applications. Experimental General information All starting materials were purchased from commercial sources and used without additional purification. Noncommercial arylacetylenes 3c and 3d were

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• as key reactants for the synthesis of natural products and their skeletons (Table 3). The complexity of these molecules requires extensive multistep pathways (ranging from 5–12 steps [127][187]), decreasing overall yields, and thus requiring further optimisation for commercial production. Narayan et

Multiple threading of a triple-calix[6]arene host

• Veronica Iuliano,
• Roberta Ciao,
• Emanuele Vignola,
• Carmen Talotta,
• Patrizia Iannece,
• Margherita De Rosa,
• Annunziata Soriente,
• Carmine Gaeta and
• Placido Neri

Beilstein J. Org. Chem. 2019, 15, 2092–2104, doi:10.3762/bjoc.15.207

• ]arene derivative 1 with bisammonium axles (e.g., 22+). In addition, we have also shown that the bis-calix[6]arene 1 was able to form pseudo[3]rotaxane architectures (e.g., 52+ in Figure 2) by double-threading with dialkylammonium axles [28]. With the aim to increase the complexity of our system we have

Analysis of sesquiterpene hydrocarbons in grape berry exocarp (Vitis vinifera L.) using in vivo-labeling and comprehensive two-dimensional gas chromatography–mass spectrometry (GC×GC–MS)

• Philipp P. Könen and
• Matthias Wüst

Beilstein J. Org. Chem. 2019, 15, 1945–1961, doi:10.3762/bjoc.15.190

• berry exocarp [8]. The biosynthesis of the diverse sesquiterpene structures in V. vinifera is, however, still largely unexplored, especially with respect to the cyclization mechanisms. Studies by Steele et al., Bülow et al., Martin et al. and theoretical studies by Tantillo show the complexity of the

Synthesis of a [6]rotaxane with singly threaded γ-cyclodextrins as a single stereoisomer

• Jason Yin Hei Man and
• Ho Yu Au-Yeung

Beilstein J. Org. Chem. 2019, 15, 1829–1837, doi:10.3762/bjoc.15.177

• discussed above, isomers I and III will both give two sets, whereas the symmetrical isomer II will give one set of triazole and CB[6] signals. The NOESY spectrum of 5R may not provide further information due to the complexity of the spectrum (Figure S14 in Supporting Information File 1), and further