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Search for "O-" in Full Text gives 2227 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides

  • Tsun-Yi Chiang,
  • Mei-Huei Lin,
  • Chun-Wei Chang,
  • Jinq-Chyi Lee and
  • Cheng-Chung Wang

Beilstein J. Org. Chem. 2025, 21, 1671–1677, doi:10.3762/bjoc.21.131

Graphical Abstract
  • modifications of bacterial polysaccharides, and the interaction of 4,6-O-pyruvylated pyranoses with lectins depends on the stereochemistry of the pyruvate ketal. Moreover, this chemical modification is crucial, as the distinct R or S diastereochemistry at the ketal center directly influences its biological
  • confirming their structure by using X-ray crystallography as direct evidence. Subsequently, the pyruvylated galactose was further applied in the synthesis of zwitterionic polysaccharide A1 (PS A1) precursor. Results and Discussion In the initial experiment, p-tolyl 2,3-di-O-acetyl-1-thio-β-galactopyranoside
  • a = 16.1017(4) Å, b = 7.7608(2) Å, c = 28.8344(8) Å, and β = 93.3680(10)°. Additionally, the presence of lattice water greatly influenced the molecular packing. The hydrogen bond (H–O–H) lengths in this lattice water ranged from 1.923 to 2.204 Å (Figure 2b). The pyruvylated galactose 6 was utilized
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Published 21 Aug 2025

Catalytic asymmetric reactions of isocyanides for constructing non-central chirality

  • Jia-Yu Liao

Beilstein J. Org. Chem. 2025, 21, 1648–1660, doi:10.3762/bjoc.21.129

Graphical Abstract
  • reductive elimination to afford INT-IV. Finally, migration of the Piv group from O to N gave the product 17a. Moreover, the Pd-catalyzed isocyanide insertion approach has been successfully extended to the generation of helical chirality [31]. As shown in Scheme 4a, phenyl diisocyanides 21 or 22 underwent
  • thionolactones, getting rid of the pre-formation of stoichiometric Ru-complexes [52][53]. Mechanistic investigations indicated that this transformation proceeds through a two-step sequence promoted by the same catalyst: 1) the diastereo- and enantioselective [3 + 2] cycloaddition to generate spiro-S,O-ketal 52
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Published 19 Aug 2025

On the aromaticity and photophysics of 1-arylbenzo[a]imidazo[5,1,2-cd]indolizines as bicolor fluorescent molecules for barium tagging in the study of double-beta decay of 136Xe

  • Eric Iván Velazco-Cabral,
  • Fernando Auria-Luna,
  • Juan Molina-Canteras,
  • Miguel A. Vázquez,
  • Iván Rivilla and
  • Fernando P. Cossío

Beilstein J. Org. Chem. 2025, 21, 1627–1638, doi:10.3762/bjoc.21.126

Graphical Abstract
  • rigid, with only small modifications on going from the ground state to the first single excited state (Figure 6). However, the presence of the two perchlorate anions results in additional coordination with Ba2+, thus resulting in larger values of the Ba–N distances, as well as of the average Ba–O and Ba
  • [33] calculations were performed using the B3LYP[34][35][36], B3LYP-D3BJ [37][38], CAM-B3LYP [39], M06 [40][41], M06-2X [42], M06-L [43][44][45], PBE0 [46] and ωB97XD [47] functionals. The 6-311+G* and 6-31++G** bases sets [48][49] were used for C, N, O, and H. The DefTZVPP [50] effective-core
  • (⟨RBa0⟩)n denote the average Ba–O bond distances (in Å) for the different crown ethers. Distances between Ba2+ and the ring points of electron density of benzene (in green) are also gathered in (B). ΔGiso and ΔGrxn terms stand for the Gibbs energies (in kcal/mol) described in Scheme 2 and have been
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Published 13 Aug 2025

Transition-state aromaticity and its relationship with reactivity in pericyclic reactions

  • Israel Fernández

Beilstein J. Org. Chem. 2025, 21, 1613–1626, doi:10.3762/bjoc.21.125

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  • associated with high barriers (>40 kcal/mol). However, we found that the Meerwein–Ponndorf–Verley-type reaction involving the double hydrogen migration from CH3–OH to O=CH2 proceeds with a much lower activation barrier of ca. 25 kcal/mol [79]. Interestingly, although the analogous reaction involving CH3–CH3
  • and O=CH2 proceeds with a much higher barrier, both transformations feature transition states whose in-plane aromaticity is nearly identical according to their NICS(3, +1) values (−24.5 ppm vs −27.2 ppm, respectively). Therefore, it is found once again that there is no clear relationship between the
  • TS-aromaticity and the barrier heights. The origin of the computed decrease of the activation barrier in the CH3–OH to O=CH2 as compared to the analogous reaction involving ethane as hydrogen donor can be initially traced to different C–H vs O–H bond strengths. Indeed, we found that the total bond
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Published 12 Aug 2025

Chemical synthesis of glycan motifs from the antitumor agent PI-88 through an orthogonal one-pot glycosylation strategy

  • Shaokang Yang,
  • Xingchun Sun,
  • Hanyingzi Fan and
  • Guozhi Xiao

Beilstein J. Org. Chem. 2025, 21, 1587–1594, doi:10.3762/bjoc.21.122

Graphical Abstract
  • ABz 7, Man PVB 8, and Man 9 through orthogonal one-pot glycosylation strategy (Scheme 1B). The 2-O-Bz group in 5–8 served as the neighboring participating group for the stereoselective construction of 1,2-trans-mannosidic bonds, while the 3-O-Lev group in 6 was the temporary protecting group for (1→3
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Published 06 Aug 2025

Thermodynamic equilibrium between locally excited and charge transfer states in perylene–phenothiazine dyads

  • Issei Fukunaga,
  • Shunsuke Kobashi,
  • Yuki Nagai,
  • Hiroki Horita,
  • Hiromitsu Maeda and
  • Yoichi Kobayashi

Beilstein J. Org. Chem. 2025, 21, 1577–1586, doi:10.3762/bjoc.21.121

Graphical Abstract
  • local excited (LE) and charge-transfer (CT) states can be experimentally observed as dual fluorescence: a structured, higher-energy emission from the LE state and a broad, red-shifted emission from the CT state [8][9]. Classical systems such as 4-(N,N-dimethylamino)benzonitrile (DMABN) and pyrene-o
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Published 05 Aug 2025

Synthesis of an aza[5]helicene-incorporated macrocyclic heteroarene via oxidation of an o-phenylene-pyrrole-thiophene icosamer

  • Yusuke Matsuo,
  • Aoi Nakagawa,
  • Shu Seki and
  • Takayuki Tanaka

Beilstein J. Org. Chem. 2025, 21, 1561–1567, doi:10.3762/bjoc.21.119

Graphical Abstract
  • , respectively [19][20]. Recently, our group established an efficient synthetic strategy for strained macrocyclic polyarenes, such as compound C, in which o-phenylene units preorganize adjacent heteroaromatics into close proximity, thereby facilitating oxidative ring-closure reactions [21]. Among these, the
  • thiophene units [24][25]. The influence of heteroaromatic positioning on the reaction outcome has been rationalized in our previous work [25]. As a further extension of this molecular design, herein we report the synthesis of an o-phenylene-pyrrole-thiophene hybrid icosamer and its oxidative fusion to yield
  • an aza[5]helicene-incorporated macrocycle. The resulting cyclophane-like structure and its optical properties have been analyzed in detail. Results and Discussion Synthesis and characterization Synthesis We obtained o-phenylene-pyrrole-thiophene hybrid icosamer 4 during our attempt to synthesize
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Published 31 Jul 2025

Facile synthesis of hydantoin/1,2,4-oxadiazoline spiro-compounds via 1,3-dipolar cycloaddition of nitrile oxides to 5-iminohydantoins

  • Juliana V. Petrova,
  • Varvara T. Tkachenko,
  • Victor A. Tafeenko,
  • Anna S. Pestretsova,
  • Vadim S. Pokrovsky,
  • Maxim E. Kukushkin and
  • Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 1552–1560, doi:10.3762/bjoc.21.118

Graphical Abstract
  • of nitrile oxides to isocyanates or their dimerization [26][27]. Since isomerization is believed to be the primary direction of molecule degradation only for bulky o,o'-disubstituted aromatic dipoles [28][29][30], the main efforts in developing a methodology were focused on suppressing dimerization
  • -substituted aromatic group, we have observed atropoisomerism (Figure 2) what is manifested by the appearance of a second set of signals in their NMR spectra. As the previously studied similar structures (Y = N–R) [22], products 5b and 5d (Y = O) were formed through the addition of a dipole molecule, resulting
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Published 31 Jul 2025

Ambident reactivity of enolizable 5-mercapto-1H-tetrazoles in trapping reactions with in situ-generated thiocarbonyl S-methanides derived from sterically crowded cycloaliphatic thioketones

  • Grzegorz Mlostoń,
  • Małgorzata Celeda,
  • Marcin Palusiak,
  • Heinz Heimgartner,
  • Marta Denel-Bobrowska and
  • Agnieszka B. Olejniczak

Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113

Graphical Abstract
  • five-membered heterocycles via [3 + 2]-cycloaddition reactions. Depending on the type of the dipolarophile used in these reactions, the target heterocycles may contain only one sulfur atom (cycloadditions with C=C or C≡C dipolarophiles) or more heteroatoms (cycloadditions with C=S, C=O, C=N, N=N, S=O
  • , N=S=O, etc. dipolarophiles) [5][6][7][8][9][10] (Scheme 1, upper part). Notably, [3 + 2]-cycloadditions of the sterically crowded thiocarbonyl S-methanide 1b with electron deficient, tetrasubstituted ethylenes activated with CN and CF3 (or CN and CO2Me) groups were encountered as the first examples
  • sulfur (χ = 2.55 (for C) and χ = 2.58 (for S) according to the Pauling scale), thiocarbonyl S-methanides 1 are considered as electron-rich 1,3-dipoles with basic and nucleophilic reactivity displayed by the =S+–CH2‒ unit [6]. Therefore, acidic compounds of type R–XH (X = NR’, O, S), which are able to
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Published 23 Jul 2025

Photoredox-catalyzed arylation of isonitriles by diaryliodonium salts towards benzamides

  • Nadezhda M. Metalnikova,
  • Nikita S. Antonkin,
  • Tuan K. Nguyen,
  • Natalia S. Soldatova,
  • Alexander V. Nyuchev,
  • Mikhail A. Kinzhalov and
  • Pavel S. Postnikov

Beilstein J. Org. Chem. 2025, 21, 1480–1488, doi:10.3762/bjoc.21.110

Graphical Abstract
  • achieved in case of o-halo-substituted diaryliodonium salts providing 64% and 67% for amides 2bg and 2bh, respectively. In contrast, iodonium salts with electron-rich aryls afforded the corresponding benzamides 2aa, 2ba, 2bb, 2bf, and 2bk in significantly lower 19–36% yields. Subsequently, various
  • not significantly change for EWG- or EDG-substituted species except for extreme cases [44]. Additionally, such reactivity pattern cannot be explained only by steric factors since the yield dramatically dropped for o-methyl-substituted iodonium salt 1f compared to o-halo-substituted salts 1g and 1h
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Published 21 Jul 2025

Copper catalysis: a constantly evolving field

  • Elena Fernández and
  • Jaesook Yun

Beilstein J. Org. Chem. 2025, 21, 1477–1479, doi:10.3762/bjoc.21.109

Graphical Abstract
  • . In their contribution, Son et al. focus on transformations via the formation of copper nitrenoids, particularly amidations via oxidative insertion to N–O bonds and reductive elimination, and a small number of other reactions. The final Review by Cho, Lee, and co-workers is useful for the scientific
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Editorial
Published 17 Jul 2025

Microwave-enhanced additive-free C–H amination of benzoxazoles catalysed by supported copper

  • Andrei Paraschiv,
  • Valentina Maruzzo,
  • Filippo Pettazzi,
  • Stefano Magliocco,
  • Paolo Inaudi,
  • Daria Brambilla,
  • Gloria Berlier,
  • Giancarlo Cravotto and
  • Katia Martina

Beilstein J. Org. Chem. 2025, 21, 1462–1476, doi:10.3762/bjoc.21.108

Graphical Abstract
  • open derivative, and the subsequent ring oxidation upon closure (as shown in the mechanism in Scheme S1 (Supporting Information File 1), the reaction mixture may contain the desired 2-substituted benzoxazole 2a together with its open-form precursor 2a-o. The latter can be hydrolysed to give N
  • -formylpiperidine and aminophenol (2a-o-hydrol) (see Figure 1a). To better understand the influence of the reaction conditions on product distribution, we plotted conversion versus selectivity in Figure 1b. Crudes were analysed by 1H NMR spectroscopy, as shown in Figure S1 (Supporting Information File 1), to
  • determine the percentage composition of starting material and products 2a, 2a-o and 2a-o-hydrol. The reaction was perfectly reproducible and no other derivatives were observed. As shown in Figure 1b, when the reaction was conducted without a catalyst, only ring opening was observed, accounting for 47%. By
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Published 15 Jul 2025

Advances in nitrogen-containing helicenes: synthesis, chiroptical properties, and optoelectronic applications

  • Meng Qiu,
  • Jing Du,
  • Nai-Te Yao,
  • Xin-Yue Wang and
  • Han-Yuan Gong

Beilstein J. Org. Chem. 2025, 21, 1422–1453, doi:10.3762/bjoc.21.106

Graphical Abstract
  • helical architectures, have attracted considerable attention due to their intrinsic chirality and tunable optoelectronic properties. Among them, nitrogen-doped helicenes (azahelicenes) and their heteroatom-co-doped counterparts – such as B/N-, O/N-, S/N-, and Se/N-doped helicenes – have emerged as highly
  • -containing helicenes, and X,N-containing helicenes (X = O, S or Se). In each section, structurally similar compounds are categorized into groups to facilitate comparison. Then, the others are discussed in chronological order based on their reported publication dates, with attribution to the respective
  • of helical aza-BODIPY analogues 43a–h, featuring a distinctive B–O–B bridge installed within each molecule [58] (Table 15). These compounds display broad chiroptical responses extending from the ultraviolet to the entire visible spectrum – an uncommon characteristic among helicene-type systems. Among
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Published 11 Jul 2025

Tautomerism and switching in 7-hydroxy-8-(azophenyl)quinoline and similar compounds

  • Lidia Zaharieva,
  • Vera Deneva,
  • Fadhil S. Kamounah,
  • Nikolay Vassilev,
  • Ivan Angelov,
  • Michael Pittelkow and
  • Liudmil Antonov

Beilstein J. Org. Chem. 2025, 21, 1404–1421, doi:10.3762/bjoc.21.105

Graphical Abstract
  • =O group of the keto tautomers [51][56]). The effects of acetone, methanol and DMSO, as seen, are based only on the increased (comparing to toluene) dielectric constant of the solvent, stabilizing in different extent the more polar KE and KK. The further increase of the polarity of the environment by
  • equilibrium towards C=O-group-containing structures. In addition, the spectra in the remaining solvents show a single band around 500 nm independent on the nature of the solvent. Obviously, these data cannot be interpreted in the frame of the concept for a tautomeric equilibrium. The rotor in 2 contains a OH
  • . It should be noted, however, that the relative stabilization of KE and KK depends, in addition, on the strength of the intramolecular hydrogen bonding. The interaction C=O···H–N is much stronger, which leads to better stabilization of KE. Some border cases of substitution in the phenyl ring of 1 are
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Published 10 Jul 2025

Reactions of acryl thioamides with iminoiodinanes as a one-step synthesis of N-sulfonyl-2,3-dihydro-1,2-thiazoles

  • Vladimir G. Ilkin,
  • Pavel S. Silaichev,
  • Valeriy O. Filimonov,
  • Tetyana V. Beryozkina,
  • Margarita D. Likhacheva,
  • Pavel A. Slepukhin,
  • Wim Dehaen and
  • Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2025, 21, 1397–1403, doi:10.3762/bjoc.21.104

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  • Vladimir G. Ilkin Pavel S. Silaichev Valeriy O. Filimonov Tetyana V. Beryozkina Margarita D. Likhacheva Pavel A. Slepukhin Wim Dehaen Vasiliy A. Bakulev TOS Department, Ural Federal University, 19 Mira str., Yekaterinburg 620002, Russia Department of Organic Chemistry, Perm State University, 15
  • thioamides 1h,i,k,n,o,s,t,v,w,y,z (general procedure). A mixture of the corresponding thioacetamide (1.0 equiv), aldehyde (1.1–4.0 equiv) and DBU (0.1 equiv or 1.0 equiv for 1h,o) in ethanol was stirred for 2–23 h at room temperature. For thioamide 1i, the reaction time was 96 h at 80 °C. The formed
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Published 10 Jul 2025

N-Salicyl-amino acid derivatives with antiparasitic activity from Pseudomonas sp. UIAU-6B

  • Joy E. Rajakulendran,
  • Emmanuel Tope Oluwabusola,
  • Michela Cerone,
  • Terry K. Smith,
  • Olusoji O. Adebisi,
  • Adefolalu Adedotun,
  • Gagan Preet,
  • Sylvia Soldatou,
  • Hai Deng,
  • Rainer Ebel and
  • Marcel Jaspars

Beilstein J. Org. Chem. 2025, 21, 1388–1396, doi:10.3762/bjoc.21.103

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  • Joy E. Rajakulendran Emmanuel Tope Oluwabusola Michela Cerone Terry K. Smith Olusoji O. Adebisi Adefolalu Adedotun Gagan Preet Sylvia Soldatou Hai Deng Rainer Ebel Marcel Jaspars Department of Chemistry, Faculty of Science, Eastern University, Vantharumoolai, Chenkalady, Sri Lanka Marine
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Published 04 Jul 2025

High-pressure activation for the solvent- and catalyst-free syntheses of heterocycles, pharmaceuticals and esters

  • Kelsey Plasse,
  • Valerie Wright,
  • Guoshu Xie,
  • R. Bernadett Vlocskó,
  • Alexander Lazarev and
  • Béla Török

Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102

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  • imidazole-based N-heterocyclic carbene (NHC)–CuCl complexes [40]. However, their synthesis is often tainted by the use of toxic reagents and solvents. In addition, when o-phenylenediamine reacts with ketones, the common catalytic methods yield benzodiazepine products [41]. In our case the reaction of o
  • -phenylenediamine and acetone was selected as a model reaction. The optimization of the reaction conditions is summarized in Table 1. All reactions were carried out at room temperature without involving any catalyst or additional solvent. While o-phenylenediamine is solid, it dissolves well in the reactant acetone
  • of catalyst- and solvent-free processes is desirable. Chalcones are a privileged scaffold in medicinal chemistry and are used for the synthesis of a multitude of products [43]. The cyclization between chalcones and hydrazines usually occur via a C=O/NH2 condensation and a subsequent NH addition to
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Published 02 Jul 2025

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

Graphical Abstract
  • tetrahedral value which results in a large ring strain of 25.5 kcal/mol, comparable to oxirane (27.3 kcal/mol) and much greater than tetrahydrofuran (5.6 kcal/mol) [4]. Moreover, the strained C–O–C bond angle effectively exposes the oxygen lone pairs, making oxetane a strong hydrogen-bond acceptor and Lewis
  • categorised into 6 synthetic strategies as depicted in Scheme 1: a) C–O bond-forming cyclisations, b) C–C bond-forming cyclisations, c) [2 + 2] cycloadditions between carbonyls and alkenes, d) ring expansions, e) ring contractions and f) O–H insertions. In the following subchapters, these strategies will be
  • discussed in more detail and illustrated by specific examples. 1.1 C–O bond-forming cyclisations 1.1.1 Intramolecular Williamson etherifications: Discovered by Alexander Williamson in 1850, this reaction is an SN2 substitution in which a leaving group, typically a halide or sulphonate ester, is displaced by
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Published 27 Jun 2025

Recent advances in amidyl radical-mediated photocatalytic direct intermolecular hydrogen atom transfer

  • Hao-Sen Wang,
  • Lin Li,
  • Xin Chen,
  • Jian-Li Wu,
  • Kai Sun,
  • Xiao-Lan Chen,
  • Ling-Bo Qu and
  • Bing Yu

Beilstein J. Org. Chem. 2025, 21, 1306–1323, doi:10.3762/bjoc.21.100

Graphical Abstract
  • (SET) process by the cleavage of the N–O bond; (c) direct homolytic cleavage of weak N–S or N–X bonds in HRP initiated in the presence of visible light; (d) the intersystem crossing (ISC) of S1 to T1 state directly from the amide anion. This review is organized by bond cleavage type, offering a deep
  • the photocatalyst [Ir(dF(CF3)ppy)2(4,4'-d(CF3)bpy)]PF6 in combination with a base (NBu4OP(O)(OBu)2) (Scheme 1) [59]. The generation of amidyl radical 5 involved a stepwise PCET process catalyzed by the combined effect, in the presence of photocatalyst and the base. Subsequently, amidyl radical 5
  • a central role in this photocatalytic system. This strategy demonstrated good chemical selectivity for the functionalization of pyridine and alkanes, resulting in 55% to 86% yields of products 38, 39, 40, and 41, respectively. Amidyl radical from N–O bond cleavage In 2022, Alexanian’s group
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Published 27 Jun 2025

Recent advances and future challenges in the bottom-up synthesis of azulene-embedded nanographenes

  • Bartłomiej Pigulski

Beilstein J. Org. Chem. 2025, 21, 1272–1305, doi:10.3762/bjoc.21.99

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  • CHCl3, AcOH and o-DCB [44]. The resulting mixture of brominated PAHs 30 and 31 was then subjected to single or double [3 + 2] annulation with various alkynes, leading to the extended structures 32 and 33. Notably, compound 33d can undergo Pd-catalysed dimerization, resulting in the formation of a chiral
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Published 26 Jun 2025

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

  • Jiangfei Chen,
  • Yi-Lin Qu,
  • Ming Yuan,
  • Xiang-Mei Wu,
  • Heng-Pei Jiang,
  • Ying Fu and
  • Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

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  • temperature, and solvents. The optimal conditions were identified as using 10 mol % Sc(OTf)3 and 2 equivalents of Ag2O at 120 °C under an argon atmosphere. The substrate scope was then evaluated using various o-alkynylarylacrylamides and alkyl nitriles under the optimized reaction conditions. Substrates with
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Published 24 Jun 2025

Synthesis of β-ketophosphonates through aerobic copper(II)-mediated phosphorylation of enol acetates

  • Alexander S. Budnikov,
  • Igor B. Krylov,
  • Fedor K. Monin,
  • Valentina M. Merkulova,
  • Alexey I. Ilovaisky,
  • Liu Yan,
  • Bing Yu and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2025, 21, 1192–1200, doi:10.3762/bjoc.21.96

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  • Alexander S. Budnikov Igor B. Krylov Fedor K. Monin Valentina M. Merkulova Alexey I. Ilovaisky Liu Yan Bing Yu Alexander O. Terent'ev N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation M. V. Lomonosov Moscow State
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Published 20 Jun 2025

Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups

  • Julius Seumer,
  • Nicolai Ree and
  • Jan H. Jensen

Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94

Graphical Abstract
  • carbon atom), and the lowest DG strength if the other two priorities are unambiguous. Figure 2 and Table 1 show examples of the results from running the program with “CCCN(C)C(=O)c1ccc(C(=O)c2ccccc2)cc1” as the input SMILES string. The sites marked with red indicate the predicted reaction sites. The
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Published 16 Jun 2025

Synthetic approach to borrelidin fragments: focus on key intermediates

  • Yudhi Dwi Kurniawan,
  • Zetryana Puteri Tachrim,
  • Teni Ernawati,
  • Faris Hermawan,
  • Ima Nurasiyah and
  • Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

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  • , successfully processing up to 15 g of starting material. Compound 93 was reduced to its corresponding aldehyde using DIBAL-H, followed by Horner–Wadsworth–Emmons (HWE) olefination with (EtO)2P(O)CH2COSEt, resulting in the unsaturated thioester 95. Reapplying the 1,4-addition reaction conditions to 95 produced
  • 70% overall yield across three steps, with a dr exceeding 98:2. The reaction continued with the reduction of thioester 98 to aldehyde 99, followed by HWE olefination with (EtO)2P(O)CH2COMe, yielding compound 100 in 92% yield (Scheme 16). The stereocontrol achieved by the catalysts was again
  • acetal in the presence of Hoveyda–Grubbs’ second-generation catalyst, affording aldehyde 112 in 75% yield as the E-isomer after a careful acidic workup. Finally, HWE olefination of aldehyde 112 with (EtO)2P(O)CHBrCN completed the synthesis of fragment 62b of borrelidin. Minnaard and Madduri emphasized
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Published 12 Jun 2025

Investigations of amination reactions on an antimalarial 1,2,4-triazolo[4,3-a]pyrazine scaffold

  • Henry S. T. Smith,
  • Ben Giuliani,
  • Kanchana Wijesekera,
  • Kah Yean Lum,
  • Sandra Duffy,
  • Aaron Lock,
  • Jonathan M. White,
  • Vicky M. Avery and
  • Rohan A. Davis

Beilstein J. Org. Chem. 2025, 21, 1126–1134, doi:10.3762/bjoc.21.90

Graphical Abstract
  • purified by the Davis group [8]. In vitro antiplasmodial image-based assay Plasmodium falciparum 3D7 were cultured in RPMI1640 (Life Technologies, Camarillo, CA, USA) supplemented with 2.5 mg/mL Albumax II, 5% AB human serum, 25 mM HEPES, and 0.37 mM hypoxanthine. Human red blood cells (RBC) (O+) were
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Published 10 Jun 2025
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