Long oligodeoxynucleotides: chemical synthesis, isolation via catching-by-polymerization, verification via sequencing, and gene expression demonstration

• Yipeng Yin,
• Reed Arneson,
• Alexander Apostle,
• Adikari M. D. N. Eriyagama,
• Komal Chillar,
• Emma Burke,
• Martina Jahfetson,
• Yinan Yuan and
• Shiyue Fang

Beilstein J. Org. Chem. 2023, 19, 1957–1965, doi:10.3762/bjoc.19.146

• on an agar plate containing kanamycin and rhamnose. As shown in Figure 4, GFP was successfully expressed. As a negative control, a portion of the culture was also plated on an agar plate containing kanamycin but not rhamnose. As expected, fluorescence of GFP was not observed. The same gene expression

• of 55% predicted in the above analysis. To demonstrate protein synthesis using genes constructed from the long synthetic ODNs, the pF1K vector containing the 800 bp GFP gene construct derived from the CBP purified 399 and 401 nt ODNs was transformed into E. coli KRX cells. Green fluorescence was

• observed upon induction using rhamnose (Figure 4). Without rhamnose induction, no fluorescence was observed. The gene expression results were identical to those using the control 800 bp GFP gene from a commercial source. Therefore, the complete process from automated long ODN synthesis, ODN purification by

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• % yields, respectively. When comparing compounds 25a and 25b, UV–vis and fluorescence studies (λmax = 500 nm, λem = 502 nm, Φem = 0.45 for 25a; λmax = 513 nm, λem = 517 nm, Φem = 0.26 for 25b; λmax = 442 nm, λem = 444 nm, Φem = 0.97 for 9,10-bis((triisopropylsilyl)ethynyl)anthracene – blue-colored) provide

• yield of 81% over the two steps. To obtain the PAH 51, a second Pd-catalyzed annulation and subsequent aromatization of 50 were performed in an acidic medium. Ultimately, the desired compound, PAH 51 bearing TIPS groups, was obtained in 82% yield as the final product. UV–vis and fluorescence studies

• demonstrated significant absorption and fluorescence characteristics. Among the synthesized compounds, linear derivative 62 exhibited the most intense absorption peak (λmax = 503 nm), whereas the other two compounds 63 and 64 possessed slightly blue-shifted absorption maxima at 487 nm and 501 nm, respectively

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• research on organic compounds exhibiting thermally activated delayed fluorescence (TADF) has led to numerous patents and research articles. This study focuses on the synthesis and investigation of the semiconducting properties of polyaromatic π-systems containing two and three fragments of pyridine-2,6

• electronic devices including OLEDs. Thus, extensive search for organic dyes exhibiting E-type fluorescence (thermally activated delayed fluorescence (TADF)) is booming [1][2][3]. The majority of research results are protected by an impressive amount of patent applications. The first example of a blue TADF

• bands and high-intensity low-energy bands. The presence of two distinct fluorescence bands is an indication of the existence of molecular conformations separated by a barrier. This is a characteristic of twisted internal charge transfer (TICT) states. It is worth of noting that the PL intensity of

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• absorption and emission maxima of 411 and 520 nm, respectively, with a mega Stokes shift of 109 nm and fluorescence quantum yields both in the solid state (41%) and in solution (86%). The optical properties were supported by computational chemistry using density functional theory for optimized geometry and

• emitter for an organic light-emitting diode through a solution process. DMB-TT-TPA (8) displayed excellent performance in both device application and photophysical properties, i.e., a maximum solution fluorescence quantum yield of 86% in THF, maximum solid-state fluorescence quantum yield of 41%, maximum

• lithiation of 7 and following reaction with dimesitylboron fluoride in 85% yield (Scheme 1). Photophysical properties The UV–vis absorption and fluorescence spectra of DMB-TT-TPA (8) were recorded in THF (Figure 1 and Table 1) [38]. It showed maximum absorption and emission wavelengths of 411 and 520 nm

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• listed in Table 2. The fitted fluorescence decay curves are shown in Supporting Information File 1 (Figure S1). For diluted solutions of 1 and 2, monoexponential lifetimes in the nanosecond timescale were observed and attributed to emission from monomeric species (6.54 and 4.14 ns, respectively). In the

• monomeric species [34]. It agrees with the intensity inversion of the vibronic absorption bands and PL redshift in the spin-coated film compared to the solution. The intensity inversion suggests formation of H-aggregates, leading to excimer fluorescence [35]. Due to the similarity to the lifetime in

• Optics USB4000 spectrophotometer. The PL spectra were collected with a Hitachi fluorescence spectrophotometer (Model F-7000) and the samples were excited at the wavelength of maximal absorption. For the PL as a function of the temperature, casting films were placed on a hot stage (Mettler Toledo FP-82

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• devices is discussed in detail. Additionally, their significance as thermally activated delayed fluorescence emitters and chromophores for OLEDs, sensors and electrochromic devices is explored. The review emphasizes the remarkable characteristics and versatility of quinoxaline derivatives in electron

• high electron mobility and efficient charge transfer. In particular, Qx derivatives find use as non-fullerene acceptors (NFAs) in OSCs and as essential building blocks in sensitizers for DSSCs. The significance of Qx extends beyond to thermally activated delayed fluorescence (TADF) emitters and

• scientific community due to their remarkable characteristics as electron-transporting and hole-blocking layers in organic electronics [60]. Moreover, these derivatives have exhibited promising traits as thermally activated delayed fluorescence (TADF) emitters. This multifaceted nature has spurred ongoing

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• twist angle between the D and A units, a strong electron deficiency of the Nz unit, and electron-donating and hole-transporting natures of carbazole, TPECNz exhibits a strong deep red emission (λem = 648 nm) with a high fluorescence quantum yield of 96%, outstanding thermal property (Tg = 236 °C), and

• designing new DR/NIR organic fluorophores in combination with device engineering to build up the performance of DR/NIR OLEDs. In general, to realize high fluorescence in the DR/NIR region from the organic fluorophores, the challenges of their pronounced non-radiative processes, and high planarity and

• energy gap between HOMO/LUMO hybrid orbits and drive fluorescence emission to longer wavelengths [48][49]. In this molecular design, the strong electron-deficient naphtho[2,3-c][1,2,5]thiadiazole (Nz) [13][50][51] as an acceptor and the strong electron-donating carbazole [52] as a donor unit were used in

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• the dipyrrin part of the macrocycle (Figure 4). The introduction of the BF2 moiety into the free-base macrocycles consequently altered the fluorescent properties of the macrocyclic systems. The appended benzo-18-crown-6 in compounds 3a–c was selective for K+, and the macrocycle fluorescence was

• alkylammonium guests. The binding constants Ka in CHCl3/MeOH 9:1 determined for 9-Zn complexes with [NH3(CH2)NH2]+, [NH3(CH2)2NH3]2+, [NH3(CH2)3NH3]2+, and [NH3CH2CH3]+ equal to 8.3·103, 6.2·103, 8.7·103, and 7.7·102 M−1, respectively, were reported. Based on the fluorescence quenching experiments the formation

• revealed a distorted ruffled molecule with a macrocycle incorporating a pyrroloindole subunit formed through the fusion between the para-phenylene ring and the pyrrolic nitrogen. 42 demonstrated fluorophore behaviour with relatively large fluorescence quantum yields of 10–20% and singlet state lifetimes of

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• individually treated with 0.15 mM, 1.5 mM, and 15 mM of CDs (CD/DPPC molar ratios 1:1, 10:1 and 100:1, respectively). Following the exposure of liposomes to CDs, the samples were incubated at 37 °C and the fluorescence signals were measured at time 0, 4, and 24 h. For each formulation, the effect of CDs was

• of CD treated liposomes is equal to 0.15 mM, 1.5 mM, and 15 mM in respect to the CD/DPPC molar ratios: 1:1, 10:1, and 100:1, respectively. The fluorescence signal was measured for each sample immediately after the exposure of LUVs to CDs and the samples were incubated at 37 °C during 24 h. For each

• formulation, a solution containing only liposomes was used as the blank solution. The membrane permeability study by fluorescence spectroscopy The membrane permeability is commonly evaluated by following the leakage of self-quenching probes such as SRB from liposomes [14]. Indeed, a fluorescence auto

Organic thermally activated delayed fluorescence material with strained benzoguanidine donor

• Alexander C. Brannan,
• Elvie F. P. Beaumont,
• Nguyen Le Phuoc,
• George F. S. Whitehead,
• Mikko Linnolahti and
• Alexander S. Romanov

Beilstein J. Org. Chem. 2023, 19, 1289–1298, doi:10.3762/bjoc.19.95

• Abstract Organic thermally activated delayed fluorescence (TADF) materials have been widely investigated due to their impressive electronic properties and applied potential for the third generation of organic light-emitting diodes (OLED). We present organic TADF material (4BGIPN) based on the strained

• : guanidine; organic; photoluminescence; TADF; yellow; Introduction Thermally activated delayed fluorescence (TADF) is a photoluminescence mechanism where excitons undergo thermally-assisted reverse-intersystem crossing from an excited triplet state to a higher-lying in energy singlet state to emit delayed

• fluorescence [1][2][3]. Organic TADF emitters have gained substantial attention in recent years for their prospective application in organic light-emitting diodes (OLEDs), photocatalysis, bioimaging, and sensors [4][5][6]. The ability to harvest both singlet and triplet excitons enable organic TADF emitters to

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• ) porphyrins were transformed to the corresponding free base and zinc(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins under standard demetallation and zinc insertion conditions. The absorption and emission properties of the obtained porphyrins were investigated by using UV–visible and fluorescence

• ; Zn-TMPP, Soret band at 425 nm) due to the extended π-conjugation after the fusion of the benzo[f]chromeno[2,3-h]quinoxaline moiety at the β-pyrrolic positions of the porphyrin macrocycle. In the fluorescence spectra, free-base benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 9–13 showed emission bands at

• ≈675 nm and 730 nm (Figure 5a). These newly synthesized free-base porphyrins displayed significant red-shifts in their emission spectra in comparison to meso-tetrakis(4-methylphenyl)porphyrin (TMPP; emission bands at ≈652 and 717 nm). Similarly, fluorescence spectra of zinc(II) benzo[f]chromeno[2,3-h

New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones

• Vladislav Yu. Shuvalov,
• Ekaterina Yu. Vlasova,
• Tatyana Yu. Zheleznova and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2023, 19, 1155–1160, doi:10.3762/bjoc.19.83

• when irradiated with UV light. Keywords: 5-aminopyrazole; azlactone; elimination; fluorescence; one-pot synthesis; pyrazolo[3,4-b]pyridin-6-one; Introduction The pyrazolo[3,4-b]pyridine scaffold is present in many biologically active compounds [1][2][3][4][5][6][7][8][9][10][11][12]. Among them, 4

• . We recorded absorption and fluorescence spectra of ethanolic solutions of compounds 4a–i, 9a, and 10a. The emission and absorption spectra of all the compounds differ slightly from each other. Their spectral parameters are presented in Table 2. In the UV spectra of ethanolic solutions of compounds 4a

• -aminopyrazoles 1, 5, 6 and azlactones 2a–i, followed by heating the resulting intermediate in DMSO in the presence of t-BuOK. Photophysical properties of the obtained compounds were studied. Biologically active 4-arylpyrazolo[3,4-b]pyridin-6-ones. Normalized absorption and fluorescence spectra of solutions of

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

• a two-photon process. DBU was found to quench the steady-state fluorescence of *PC1 with a quenching rate constant two orders of magnitude smaller than the diffusion rate constant in DMSO at 298 K and one order of magnitude greater under the borylation reaction conditions (i.e., 0.20 M DBU) than the

The effect of dark states on the intersystem crossing and thermally activated delayed fluorescence of naphthalimide-phenothiazine dyads

• Liyuan Cao,
• Xi Liu,
• Xue Zhang,
• Jianzhang Zhao,
• Fabiao Yu and
• Yan Wan

Beilstein J. Org. Chem. 2023, 19, 1028–1046, doi:10.3762/bjoc.19.79

• –acceptor dyads were prepared to study the thermally activated delayed fluorescence (TADF) properties of the dyads, from a point of view of detection of the various transient species. The photophysical properties of the dyads were tuned by changing the electron-donating and the electron-withdrawing

• capability of the PTZ and NI moieties, respectively, by oxidation of the PTZ unit, or by using different aryl substituents attached to the NI unit. This tuning effect was manifested in the UV–vis absorption and fluorescence emission spectra, e.g., in the change of the charge transfer absorption bands. TADF

• was observed for the dyads containing the native PTZ unit, and the prompt and delayed fluorescence lifetimes changed with different aryl substituents on the imide part. In polar solvents, no TADF was observed. For the dyads with the PTZ unit oxidized, no TADF was observed as well. Femtosecond

A fluorescent probe for detection of Hg²⁺ ions constructed by tetramethyl cucurbit[6]uril and 1,2-bis(4-pyridyl)ethene

• Xiaoqian Chen,
• Naqin Yang,
• Yue Ma,
• Xinan Yang and
• Peihua Ma

Beilstein J. Org. Chem. 2023, 19, 864–872, doi:10.3762/bjoc.19.63

• that TMeQ[6] and G form an inclusion complex with a host–guest ratio of 1:1 and the equilibrium association constant (Ka) was 2.494 × 104 M−1. The G@TMeQ[6] fluorescent probe can sensitively recognize Hg2+ ions by fluorescence enhancement. The linear range is 0.33 × 10−5–1.65 × 10−5 mol·L−1, R2

• + ions [34]. Because of the synergistic combination of Q[8], SQ2 and Hg2+ ions, it shows fluorescence quenching. Cong's group found that Q[7] can encapsulate the benzimidazole part of N-(2-benzimidazolylmethyl)-N,N-bis(2-pyridylmethyl)amine cation (BIBPA+) to construct a host–guest fluorescent probe. The

• change in fluorescence intensity can be used for the recognition of Cd2+ and Zn2+ ions [35]. The symmetric tetramethyl cucurbit[6]uril (TMeQ[6]) is one of the earliest characterized modified cucurbit[6]urils [36]. Compared with Q[6], tetramethyl cucurbit[6]uril (TMeQ[6]) has good solubility in water

Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities

• Yuan-Nan Yuan,
• Jin-Qiang Li,
• Hong-Bin Fang,
• Shao-Jun Xing,
• Yong-Ming Yan and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59

• cytometry (BD, USA). CD8+ T cells and Panc02-h7-GP-GFP cells were co-cultured with the corresponding concentrations of compounds or DMSO for 18 h. Fluorescence intensity was measured using a microplate reader (emission at 476 nm, excitation at 514 nm). Anti-inflammatory assay RAW264.7 (a mouse macrophage

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• HPLC. Due to the large conjugated structure, NG 110 exhibited a significantly red-shifted emission in the near-infrared (NIR) region. Furthermore, the structure extension causes significant improvements both in the fluorescence quantum yield and CPL properties. The dissymmetry factors glum of (P)- and

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

• Semyon V. Tsybulin,
• Ekaterina A. Filatova,
• Alexander F. Pozharskii,
• Valery A. Ozeryanskii and
• Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

• of compounds 5d,e and 6d,e is likely a reflection of the elongation of the conjugation chain. This also supports the conjugation pathway between the nitro group and the more distant dimethylamino group of DMAN fragment marked in blue in Figure 7. All synthesized oligomers 5 display no fluorescence in

• solution (chloroform and acetonitrile were tested). For comparison, N,N-dimethyl-4-((4-nitrophenyl)ethynyl)aniline demonstrates a weak fluorescence with an emission maximum at 550 nm (EtOH) [37]. The optical band gaps (Egopt), estimated from the onset point of the absorption spectra, ranged within 2.39 eV

Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles

• Deepak Singh,
• Shyamal Pramanik and
• Soumitra Maity

Beilstein J. Org. Chem. 2023, 19, 666–673, doi:10.3762/bjoc.19.48

• ]. Finally, the reaction of 5 with benzoic acid and zinc acetate (in a 1:1 ratio) under standard reaction protocol resulted in the competitive formation of products 4a and 10 (Scheme 3E), indicating the susceptibility of other acids towards this method. These results, along with the Stern–Volmer fluorescence

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• in the presence of TBTQ-C6 was greatly improved. In addition, the fluorescence of CS-TPE was significantly enhanced by introducing TBTQ-C6, and remained relatively stable with variations in pH for both CS-TPE and TBTQ-C6/CS-TPE. Such pH-responsive supramolecular spherical nanoparticles with stable

• fluorescence emission based on CS-TPE or TBTQ-C6/CS-TPE may find applications in various fields, including the development of visual oral drug delivery systems. Keywords: chitosan; nanoparticle; tetraphenylethylene; tribenzotriquinacene; Introduction Stimuli-responsive assemblies in aqueous media have drawn

• , conventional fluorescent dyes exhibit aggregation-caused quenching (ACQ) when introduced into nanoparticles at high loads, resulting in poor fluorescence imaging quality. In recent years, tetraphenylethylene (TPE)-based dyes have been frequently used to overcome the ACQ problem due to their unique aggregation

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

• a pH-dependent excimer formation that is significantly red-shifted relative to the pyrene and phenanthridine fluorescence. While the conjugate with a short linker showed negligible spectrophotometric changes due to the polynucleotide addition, the conjugate with a longer and more flexible linker

• exhibited a micromolar and submicromolar binding affinity for ds-polynucleotides and inactivated a mutant of dipeptidyl peptidase enzyme E451A. Confocal microscopy revealed that the conjugate with the longer linker entered the HeLa cell membranes and blue fluorescence was visualized as the dye accumulated

• signalize complex formation (interaction with a biomolecule, cyclodextrine, metal cation, etc.) or change of receptor conformation [5][6]. Employment of pyrene as a biosensor is complicated due to its large aromatic surface's hydrophobicity and fluorescence sensitivity to oxygen. Therefore, modifications of

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• fluorescence spectra. Synthesis of meso-triazole-bridged porphyrin conjugates In recent years, many chromophoric moieties have been introduced at the meso-position of porphyrins by implying diverse synthetic procedures. Among these, the CuAAC click-mediated reactions are proving to be a popular choice for the

• a photophysical investigation, a weak interaction was observed between two subunits at ground state in porphyrin-ferrocene dyads. Also, the fluorescence of porphyrin was significantly quenched in porphyrin-ferrocene conjugates due to photoinduced electron transfer from ferrocene to porphyrin

• protocol in a 42% yield by using CuI and DIPEA in THF at room temperature (Scheme 11). Their photophysical studies revealed that the fluorescence of zinc porphyrin 58 is strongly quenched due to the copper-corrole 59 in the dyad 60. Also, an efficient excited-state interaction was found between zinc

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

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

• visualized by their fluorescence under UV–lamp (λ = 245 and 365 nm) or staining with iodine vapor or 15% H2SO4 or KMnO4 solution, or Ce(IV)SO4 in H2SO4. Melting points were determined on a Gallenkamp apparatus UK and are uncorrected. NMR spectra were recorded on a Bruker 600 MHz spectrometer at the central

Formal total synthesis of macarpine via a Au(I)-catalyzed 6-endo-dig cycloisomerization strategy

• Jiayue Fu,
• Bingbing Li,
• Zefang Zhou,
• Maosheng Cheng,
• Lu Yang and
• Yongxiang Liu

Beilstein J. Org. Chem. 2022, 18, 1589–1595, doi:10.3762/bjoc.18.169

• -inflammatory [4][5][6][7][8], insecticidal, fungicidal, etc [9]. In addition to the above-mentioned activities, macarpine was also used as a DNA probe for flow cytometry and fluorescence microscopy due to its fluorescent properties [10]. Despite some research on the activities of macarpine had been performed