Molecular tweezer–peptide conjugates disrupt the protein–protein interaction between survivin and histone H3 essential in mitosis

• Catherine Gsell,
• Philipp Rebmann,
• Karina Opara,
• Christine Beuck,
• Peter Bayer,
• David Bier,
• Ingrid R. Vetter and
• Thomas Schrader

Beilstein J. Org. Chem. 2026, 22, 557–567, doi:10.3762/bjoc.22.41

• ) calcium ion with amino acid side chains – that might also be in part be responsible for the lack of tweezer binding to Lys-121 – but also represents a new binding mode for the tweezer moiety. The (hydrated) Ca2+ ion is apparently too large to enter the cavity of the tweezer ring, in contrast to larger Cs

• 2b on K-121 leaves more room for stabilizing packing effects. Lys-122 is also located in the vicinity of the H3-T3ph binding site; although it forms a protein contact with Asn-118, there is plenty of room around it in the crystal structure (Figure 4). However, to target this amino acid, the linker

Experimental and DFT studies on the regioselective methanolysis of 5-azido-9-oxabicyclo[6.1.0]nonan-4-yl 4-nitrobenzoate isomers

• İlknur Polat,
• Selçuk Eşsiz and
• Emine Salamci

Beilstein J. Org. Chem. 2026, 22, 547–556, doi:10.3762/bjoc.22.40

• , pharmaceutical compounds, and chiral ligands. The Lewis acid-catalyzed ring-opening reaction of cyclohexene oxide by MeZH (Z = O, S, and NH) is well known [20]. However, studies on large-sized bicyclic epoxides remain relatively limited in the published literature. In our previous study, we performed the ring

• each elementary reaction step along these routes were computed. The acid-mediated ring-opening reaction in the isomeric epoxides 9, initiated by protonation, can follow two possible pathways – either along the intermediate 12 or along the intermediate 15. There is a possibility of two products being

Melifoliox B, a novel phloroglucin derivative isolated from Melicope barbigera (Rutaceae) and synthesis of new oxidation products from melifoliones A and B

• Horst Weber,
• Kim-Thao Tran-Cong,
• Bernhard Mayer,
• Guido J. Reiss,
• Iryna S. Konovalova,
• Marc S. Appelhans,
• Kenneth R. Wood and
• Claus M. Passreiter

Beilstein J. Org. Chem. 2026, 22, 535–546, doi:10.3762/bjoc.22.39

• synthesis of 4 and its possible isomer 3, the required compounds 1 and 2 were synthesized as a mixture of the isomers starting from chromene 5, briefly heated in a closed microwave apparatus with catalytic amounts of acetic acid. Forced heating of 5 in acetic acid or use of stronger acids lead to the

• made to cyclize 5 into melifolione B (2) with the following results (Scheme 1) Heating of 5 in DMF at 100 °C yielded melifolione A (1) with traces of melifolione B (2). When 5 was heated in acetic acid at 80 °C, only benzoxocin 6 could be isolated. Reaction of 5 with catalytic amounts of p

• -toluenesulfonic acid at 80 °C in toluene afforded benzoxocin (7) as the only product. On the other hand, melifolione A (1) was completely decomposed under these conditions. Irradiation of 5 in methanol with UV-light (300 nm) for 3 days at room temperature gave melifolione B (2) with traces of melifolione A (1

Modern synthetic pathways towards eribulin and its subunits

• Sebastian Dominik Graf

Beilstein J. Org. Chem. 2026, 22, 495–526, doi:10.3762/bjoc.22.37

• modern approaches towards the key fragments and total synthetic strategies for 1 in recent years. Review In 2016, Konda and co-workers reported two approaches for the assembly of the tetrasubstituted tetrahydrofuran unit of 1 (Scheme 2 and Scheme 3) [72]. For the first path, (S,S)-tartaric acid (13) was

• used as a starting material and was protected as acetonide within the first step to enable the reduction of both acid moieties towards 14 (Scheme 2). Bn-protection, followed by oxidation and olefination yielded sulfone 15, which was vinylated leading to 16 as a single diastereomer. Further Grubbs

• the secondary alcohol unit of 71 was changed via oxidation and stereospecific reduction, then 1,4-reduction of the enone and treatment with camphorsulfonic acid led to fully cyclized intermediate 72 as a single isomer. During this process the acetate groups were cleaved off and had to be reinstalled

Synthesis and uranyl(VI) extraction performance of a calix[4]pyrrole–tetrahydroxamic acid receptor

• Sara Karnib,
• Rana Baydoun,
• Wissam Zaidan,
• Nancy AlHaddad,
• Omar El Samad,
• Bilal Nsouli,
• Francine Cazier-Dennin and
• Pierre-Edouard Danjou

Beilstein J. Org. Chem. 2026, 22, 486–494, doi:10.3762/bjoc.22.36

• extractants. Here, we report the design and synthesis of PCP HA, a phenoxycalix[4]pyrrole scaffold functionalized with four hydroxamic acid (HA) groups, and evaluate its uranium(VI) extraction potential. PCP HA was synthesized from its ester precursor (PCP E) via hydroxyaminolysis using KOH, achieving a 95

• , removing up to 95% of uranyl(VI) from aqueous solutions (1 mM) at acidic pH, likely due to the strong coordination provided by its hydroxamic acid groups. Further studies revealed that the extraction efficiency also depends on the ligand-to-metal molar ratio. These findings establish PCP HA as a promising

• supramolecular material for the removal of uranyl from aqueous media. Keywords: gamma spectroscopy; hydroxamic acid; phenoxycalix[4]pyrrole; solid–liquid extraction; uranyl(VI) extraction; Introduction Over the past few decades, supramolecular chemistry has advanced intensively establishing itself as a central

Synthesis of a HDAC inhibitor–nanogold probe for cryo-EM visualization in class I HDAC co-repressor complexes

• Wiktoria A. Pytel,
• John W. R. Schwabe and
• James T. Hodgkinson

Beilstein J. Org. Chem. 2026, 22, 480–485, doi:10.3762/bjoc.22.35

• routes (Scheme 1) [14][15][18]. Intermediates 5–7 were prepared in a manner analogous to Smalley et al. [14]. The first step in the linker synthesis for Au–(CI-994) involved a monoprotection of nonanedioic acid with a benzyl group to give 5 which proceeded in moderate yield due to the formation of the

• dibenzylated by-product. Compound 5 was then coupled to the CI-994 intermediate 3 via HATU-mediated amide bond formation to produce 6 in good yield. Removal of the benzyl protecting group was performed by catalytic hydrogenation and acid 7 was obtained in near quantitative yield. Intermediate 7 was converted

Recent advances in the stereoselective synthesis of distal biaxially chiral molecules

• Fanxing Zhou,
• Chen Zhang,
• Lingyu Sun,
• Yiyun Fang,
• Siming Zheng,
• Lina Hu,
• Mengyang Shen,
• Zhen Zhao,
• Wei Xu,
• Yunqiang Sun and
• Zi-Qiang Rong

Beilstein J. Org. Chem. 2026, 22, 461–479, doi:10.3762/bjoc.22.34

• carboxylic acid derivatives (Scheme 2b) [43]. They revealed that ortho-alkoxy substitution on the benzene-derived alkyne markedly enhanced both reactivity and enantioselectivity, while incorporation of a naphthyl substituent into the diyne enabled access to remote biaxially chiral molecules. Subsequent

• studies have further broadened the synthetic toolbox for remote biaxial chirality. Du and co-workers designed a series of chiral phosphoric acid catalysts derived from protected axially chiral diols 13, employing a boronic acid-mediated coupling strategy to construct remote biaxially chiral phosphoric

• polarized BOP bis(2-oxo-3-oxazolidinyl)phosphonic substituent and the extended π system in the arylboronic acid coupling partner. In 2018, Razler and co-workers described an approach for the synthesis of an architecturally complex API 57 having multiple chiral axes (Scheme 14) [53]. Their strategy relied on

Structural reassignment of compound 968, an allosteric glutaminase inhibitor

• Lindsey A. Albertelli,
• Sainabou Jallow,
• Chun Li and
• Scott M. Ulrich

Beilstein J. Org. Chem. 2026, 22, 455–460, doi:10.3762/bjoc.22.33

• . Glutaminases catalyze the hydrolysis of glutamine to glutamate, which supports the biosynthesis of amino acids, lipids, and glutathione and can also be oxidatively deaminated to α-ketoglutarate and enter the citric acid cycle. The “glutamine addiction” of cancer cells has made glutaminase an attractive

A facile and practical method for the synthesis of trans-(±)-taxifolin and its derivatives via Darzens reaction

• Bo Peng,
• Panpan Yang,
• Maaz Khan,
• Xiaotong Lin,
• Jiang Wu,
• Peng Fu and
• Qingqing Wu

Beilstein J. Org. Chem. 2026, 22, 443–450, doi:10.3762/bjoc.22.31

• with 2,4,6-trihydroxyacetophenone as a starting material undergoing hydroxy protection, α-bromination, construction of α,β-epoxy carbonyl products via the Darzens reaction, acid-mediated deprotection, and cyclization to afford the target compounds. This method is highlighted by satisfactory overall

• -epoxycarbonyl intermediates. The latter undergo simultaneous deprotection and cyclization by treatment with acid to afford the targeted trans-(±)-taxifolin and its derivatives [19][20][21][22][23][24][25][26][27][28][29][30] (Scheme 1a). Although this synthetic route is efficient, a significant drawback is that

• via Darzens reaction. Subsequent acid-mediated deprotection and cyclization then afforded the target compounds. Compared with the widely used method involving peroxides reported earlier, the present method is highlighted with avoidance of the use of peroxides, therefore enabling safe scale-up and

Synthesis and stereochemical analysis of dynamic planar chiral oxa[7]orthocyclophene

• Yukiho Hashimoto,
• Yuuya Kawasaki,
• Kazunobu Igawa and
• Katsuhiko Tomooka

Beilstein J. Org. Chem. 2026, 22, 436–442, doi:10.3762/bjoc.22.30

• -alkene 7 in 81% yield. The hydroxy group of 7 was substituted with chlorine using oxalyl chloride in DMF, and the TIPS group was removed by treatment with hydrochloric acid to afford the chloroalcohol 2a (74% yield in two steps). After several attempts to cyclize compound 2a via Williamson etherification

Synthesis and anti-cancer activity of naphthalimide–organylselanyl conjugates

• Rajkumar Ravi and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2026, 22, 416–435, doi:10.3762/bjoc.22.29

• compounds, selenoproteins, incorporating selenocysteine, the 21st amino acid, are of special importance due to their essential role in various biochemical processes [16][17]. Inspired by natural biosynthetic pathways, synthetic chemists have developed novel low-molecular-weight organoselenium compounds

• methylseleninic acid (1) has emerged as a promising drug candidate for the treatment of triple-negative breast cancer (TNBC) [27]. In addition, the classical organoselenium compound diphenyl diselenide (2) has shown significant anticancer activity against the MDA-MB-231 breast cancer cell line [28]. Very recently

• significant negative character that enables it to form a hydrogen bonding interaction with the active site amino acid residue of the proteins. MEP analysis of compounds 7 and 8 The molecular electrostatic potential (MEP) maps of compounds 7 and 8 are depicted in Figure 6a and 6b, respectively. The MEP

Cone p-aminocalix[4]arenes enriched with ‘clickable’ alkyne or azide functionalities

• Ilia Korniltsev,
• Vasily Bazhenov,
• Alexander Gorbunov,
• Dmitry Cheshkov,
• Stanislav Bezzubov,
• Vladimir Kovalev and
• Ivan Vatsouro

Beilstein J. Org. Chem. 2026, 22, 399–415, doi:10.3762/bjoc.22.28

• persilylated propargyl ethers 7–10 from precursors 2–5 (Scheme 1). Expectedly, (ipso-)nitration of calixarenes 6–10 by mixtures of fuming nitric acid and glacial acetic acid in dichloromethane solutions could potentially be complicated by both the incomplete conversion of the starting materials and also by

• formation of side products, due to acid-promoted cleavage and undesired transformations of the TBS-protected propargyl groups and/or due to unwanted oxidation/nitration of the calixarene core [93]. Indeed, nitration of calixarene 6 has been reported to furnish the desired wide-rim exhaustively nitrated

• calix[4]arene 11 having four TBS-protected propargyl groups at the narrow rim in only moderate yield of 37% [9]. In our hands, according to the NMR spectra of the reaction mixture, under the reported conditions (>30 equiv of fuming HNO3 per calixarene aromatic unit in a 1:1 dichloromethane/acetic acid

Design, synthesis and biological evaluation of 2,5-diaryloxazolo[4,5-d]pyrimidin-7-ylamines as selective cytotoxic agents against HeLa cells

• Maryna V. Kachaeva,
• Agnieszka B. Olejniczak,
• Marta Denel-Bobrowska,
• Victor V. Zhirnov,
• Yevheniia S. Velihina,
• Stepan G. Pilyo and
• Volodymyr S. Brovarets

Beilstein J. Org. Chem. 2026, 22, 390–398, doi:10.3762/bjoc.22.27

• the human body could be realized and are presented in Table 5. According to Table 5, compound 1 is expected to interact with three nucleic acid receptors and three stress signaling pathways with high probability. However, the cytotoxicity of compounds 7 and 9 is likely not due to interactions with the

Dialkylaminoalkylation of β-ketosulfones via ring-opening of 3-sulfonylpyrrolidines

• Evgeny M. Buev,
• Alexander V. Pavlushin,
• Vladimir S. Moshkin and
• Vyacheslav Y. Sosnovskikh

Beilstein J. Org. Chem. 2026, 22, 383–389, doi:10.3762/bjoc.22.26

• ] cycloaddition of azomethine ylides at various vinyl sulfones were well studied [38][39][40][41], a method for the preparation of 3-sulfonylpyrrolidines from β-ketosulfones was previously unknown. We synthesized a number of pyrrolidines 2a–f in 83–97% yield, which were purified by an acid-base extraction (Scheme

• 4q–t in 61–87% yields. It should be noted that the leaving 3-benzoyl group formed a methyl benzoate when the reactions were performed in methanol. We also observed the formation of S-butyl benzothioate in the reaction mixture in case of 4q. These by-products were readily removed by an acid-base

Electrosynthetic access to unsymmetrical oxaza[8]helicenes with high chiral stability and strong circularly polarized luminescence (CPL)

• Tin Zar Aye,
• Rubal Sharma,
• Muthu Karuppasamy,
• Daiya Suzuki,
• Haruka Nakajima,
• Yoshitane Imai,
• Mitsuhiro Arisawa,
• Mohamed S. H. Salem and
• Shinobu Takizawa

Beilstein J. Org. Chem. 2026, 22, 372–382, doi:10.3762/bjoc.22.25

• unsymmetrical oxaza[8]helicenes Building on Zhang’s facile acid-mediated carbazole synthesis [53], in which aniline derivatives react with p-benzoquinone to afford 3-hydroxycarbazoles [54], we employed a closely related substrate. Specifically, N-(p-tolyl)phenanthren-3-amine (2) – prepared from 3

• -bromophenanthrene (1) via Buchwald–Hartwig amination with p-toluidine under Pd catalysis [55] – was subjected to phosphoric acid-mediated annulation with p-benzoquinone to give the hydroxycarbazole derivative 3 through a tandem Michael addition/ring-closure sequence. After rapid optimization of key parameters (see

• structures). Aromaticity of oxaza[8]helicenes: (A) NICS(0)zz and NICS(1)zz values of 5a and 5b calculated at MN15/6-311G(2d,p)/SMD=chloroform level of theory; (B) ACID plots calculated at the B3LYP/6-311G(d,p) level of theory (isosurface value: 0.05). (P/M) Enantiomerization process of 5a (A), 5b (B), 6a (C

Recent advances in the cleavage of non-activated amides

• Eun-Sol Choi and
• Hyo-Jun Lee

Beilstein J. Org. Chem. 2026, 22, 352–369, doi:10.3762/bjoc.22.23

• of conventional, non-activated amides remains far more difficult. This review summarizes recent advances over the past decade in the activation and cleavage of non-activated amide C–N bonds for their conversion into diverse carboxylic acid derivatives. Key strategies covered include transition-metal

• secondary and tertiary amides with octanol catalyzed by CeO2, utilizing the advantage of its cooperative acid–base functionalities (Scheme 2) [46]. Under the optimized conditions, N,N-dimethylbenzamide (3) and N,N-diethylbenzamide (4) were smoothly converted to octyl benzoate (1) in 93% and 95% yield

• of CeO2 to attack the carbonyl carbon, leading to cleavage of the C–N bond (B). Subsequent nucleophilic attack of the octoxide anion on the activated carbonyl center (C) then furnishes the ester product. Later, the same group found that niobium could also serve as a heterogeneous Lewis acid catalyst

Synthesis of tricyclic fused pyrrolidine nitroxides from 2-alkynylpyrrolidine-1-oxyls

• Mark M. Gulman,
• Yuliya F. Polienko,
• Sofia Yu. Trakhininа,
• Yuri V. Gatilov,
• Tatyana V. Rybalova,
• Sergey A. Dobrynin and
• Igor A. Kirilyuk

Beilstein J. Org. Chem. 2026, 22, 344–351, doi:10.3762/bjoc.22.22

• that this methylene fragment has a more fixed conformation, consistent with the annulated structure (Figure 4). Nitroxides are known to decay in biological systems; the major mechanism is chemical reduction with cellular antioxidants (ascorbic acid and glutathione) and enzymatic systems [34]. The rate

Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis

• Nicolas Kratena,
• Nicolas Heinzig and
• Peter Gärtner

Beilstein J. Org. Chem. 2026, 22, 289–343, doi:10.3762/bjoc.22.21

• the activation of the diphosphate group and ionisation) [25][37] and Class II (ionisation by olefin or epoxide protonation via a carboxylic acid in the active site) [26][38][39] and their reactions thus are mediated by carbocations and olefins, through careful preorganisation of the linear substrate

• found in pseudolaric acid B (14) biosynthesis [64][65]. In this case, the linear precursor 12 is first cyclised to give intermediate 14a akin to the α-terpinyl cation (see Scheme 3). From here, quantum chemical calculations indicate that the subsequent 1,2-alkyl shift and olefin cyclisation occur in a

• the methyl groups residing at C-4 and the C-7 methylene to ent-7α-hydroxykaurenoic acid (34a). The hydroxy group in 34a can further engage with a CYP450 enzyme at C-6 (different CYP isoforms responsible in different genii) to form an alkyl radical 34b which upon further SET forms an intermediate

Spirobarbiturates with a pyrrolizidine moiety: synthesis, structure and biological evaluation

• Arthur A. Puzyrkov,
• Andrew S. Drachuk,
• Ekaterina A. Popova,
• Alexander V. Stepakov and
• Vitali M. Boitsov

Beilstein J. Org. Chem. 2026, 22, 274–288, doi:10.3762/bjoc.22.20

• ; pyrrolizidine moiety; spirobarbiturates; three-component reactions; Introduction The history of barbiturates dates back to 1863, when the young Adolf von Baeyer first synthesized barbituric acid [1][2]. In 1903, the drug marketed under the trade name barbital (veronal©) became commercially available as a

• sedative [3]. For more than 120 years of barbiturate history a lot has happened. Barbituric acid-based medications were widely used until the 40–50s of the last century. Then, due to accumulating evidence of their addictive potential and adverse effects, most of these substances were eventually phased out

• ]. In 2018, Kota and Sreevani prepared spirobarbiturates via a Mo(CO)6-catalyzed intermolecular [2 + 2 + 2] cycloaddition of propargyl halides with dipropargylbarbituric acid [24]. Almeida and colleagues described the formation of spiroindoline barbiturates via thermal rearrangement of 2,1-benzisoxazole

Arene activation via π-bond localization: concepts and opportunities

• Paul Meiners,
• Julian J. Melder and
• Tobias Morack

Beilstein J. Org. Chem. 2026, 22, 257–273, doi:10.3762/bjoc.22.19

• established a mechanistic foundation for exploiting η3-benzyl intermediates as conduits for controlled arene-to-cyclohexadiene conversion. Building on this foundational discovery, Bao and Yamamoto subsequently broadened the nucleophile scope to encompass allylsilanes [76], allylboronic acid derivatives [77

A mild and atom-efficient four-component cascade strategy for the construction of biologically relevant 4-hydroxyquinolin-2(1H)-one derivatives

• Dmitrii A. Grishin,
• Kseniia I. Sharkovskaia,
• Ilya G. Kolmakov,
• Daria A. Ipatova,
• Rostislav A. Petrov,
• Nikolai D. Dagaev,
• Dmitry A. Skvortsov,
• Maria G. Khrenova,
• Valeriy V. Andreychev,
• Sergei A. Evteev,
• Yan A. Ivanenkov,
• Roman L. Antipin,
• Olga А. Dontsova and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2026, 22, 244–256, doi:10.3762/bjoc.22.18

• and selective synthesis of previously inaccessible 4-hydroxyquinolin-2(1H)-one derivatives. Utilizing readily available 6-halo-4-hydroxyquinolinones, aromatic aldehydes, Meldrum’s acid, and alcohols under ʟ-proline catalysis, the reaction proceeds via in situ formation of arylidene-substituted Meldrum

• direct access to scarcely explored open-chain quinolinone esters, expanding the medicinal chemistry toolbox with promising scaffolds for drug discovery. Keywords: antibacterial activity; 4-hydroxyquinolin-2(1H)-one; ʟ-proline catalysis; Meldrum’s acid; Michael addition; multicomponent reaction

• -hydroxyquinoline scaffolds bearing both C6-halogen and γ-(3,4-dimethoxyphenyl)propanoic acid motifs. Existing approaches to such derivatives comprise typically multiple steps, are limited in scope, or require harsh reaction conditions, restricting their application in rapid analogue generation. The combination of

Conformational analysis of difluoromethylornithine: factors influencing its gas-phase and bioactive conformations

• Matheus P. Freitas

Beilstein J. Org. Chem. 2026, 22, 237–243, doi:10.3762/bjoc.22.17

• intermolecular interactions in biological environments. This study clarifies the electronic origin of DFMO’s gauche effect and provides insight into how local electronic factors determine the structure of fluorinated amino acid derivatives. Keywords: conformational analysis; difluoromethylornithine; gauche

• balance shifts, since strong intermolecular interactions – especially hydrogen bonding with amino acid residues – favor a type-II geometry as the predominant bioconformation. Nevertheless, when different conformers engage in comparable intermolecular interactions, intramolecular effects such as the gauche

• amino acid residues and water molecules, while the ligand is delineated by a contour line to distinguish it from the binding cavity. Lowest-energy type-I, type-II, and type-III conformers of the zwitterionic form of (S)-DFMO. Color labels: H = blue, C = pink, N = orange, O = red, F = yellow. DFT

Configuration–packing synergy enabling integrated crystalline-state RTP and amorphous-state TADF

• Ruiyan Wang and
• Yunan Wu

Beilstein J. Org. Chem. 2026, 22, 224–236, doi:10.3762/bjoc.22.16

• Technology Co., Ltd.; 3-(9H-carbazol-9-yl)phenylboronic acid (5) was obtained from Sukailu Co., Ltd.; glacial acetic acid, anhydrous sodium sulfate, dichloromethane, n-hexane, ethanol, chloroform, and tetrahydrofuran were supplied by Guangzhou Chemical Reagents Co., Ltd. All reagents were used as received

• placed into a 250 mL three-necked round-bottomed flask, ensuring the proper amount of space for the reaction. It was then dissolved in 100 mL of glacial acetic acid, which served as the solvent. To create an inert atmosphere and prevent any unwanted reactions with oxygen, the solution was purged with

• no moisture or oxygen interfered with the reaction. Following this, 3-(9H-carbazol-9-yl)phenylboronic acid (5, 1.09 g, 3.80 mmol) was added to the flask. The mixture was stirred for 5 minutes to allow proper mixing. To facilitate the Suzuki coupling reaction, an aqueous solution of potassium

Synthesis of diaryl phosphates using phytic acid as a phosphorus source

• Kazuya Asao,
• Seika Matsumoto,
• Haruka Mori,
• Riku Yoshimura,
• Takeshi Sasaki,
• Naoya Hirata,
• Yasuyuki Hayakawa and
• Shin-ichi Kawaguchi

Beilstein J. Org. Chem. 2026, 22, 213–223, doi:10.3762/bjoc.22.15

• Research, Saga University, 152-1 Shonan-cho, Karatsu, Saga 847-0021, Japan Nippon Concrete Industries Co., Ltd., 4-6-14 Shibaura, Minato-ku, Tokyo 108-8560, Japan 10.3762/bjoc.22.15 Abstract Phytic acid is a phosphorus-rich molecule, which is produced by plants using water-soluble phosphates absorbed from

• soil. It can potentially serve as a phosphorus source in the syntheses of organic phosphates; however, this approach has not been utilized for the preparation of phosphate esters. In this study, we report the first successful synthesis of phosphate esters using phytic acid as a phosphorus source. Crude

• products of phosphate diesters were obtained through the reactions of commercially available phytic acid and aromatic alcohols with 31P nuclear magnetic resonance yields up to 83%. We also isolated a portion of the reaction substrates with yields up to 60%. Next, we extracted phytic acid from rice bran

Base-promoted deacylation of 2-acetyl-2,5-dihydrothiophenes and their oxygen-mediated hydroxylation

• Vladimir G. Ilkin,
• Margarita Likhacheva,
• Igor V. Trushkov,
• Tetyana V. Beryozkina,
• Vera S. Berseneva,
• Vladimir T. Abaev,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2026, 22, 192–204, doi:10.3762/bjoc.22.13

• ] and more complex molecules [11]. Rearrangements of the oxidized compounds are equally important transformations [12]. Oxidation of compounds containing a carbonyl group into carboxylic acid derivatives can be divided into two large groups: direct oxidation and oxidative rearrangements. Direct

• ]. Bernini et al. have developed a catalytic system, containing hydrogen peroxide/methyltrioxorhenium and an ionic liquid, to oxidize acetophenones to afford phenols [20]. Junjappat et al. found that hydrogen peroxide activated by boric acid can act as oxidant for the direct conversion of aromatic ketones to

• yield (21%, Table 1, entry 2). When acid (HCl) was added after quenching the residue with water, the yields of products 2a and 3a were increased (30 and 35%, Table 1, entry 3). The selective formation of 2-hydroxy-2,5-dihydrothiophene 2a in 41% yield was achieved when using 5 equiv of sodium and 0.25 mL