Ni-promoted reductive cyclization cascade enables a total synthesis of (+)-aglacin B

• Si-Chen Yao,
• Jing-Si Cao,
• Jian Xiao,
• Ya-Wen Wang and
• Yu Peng

Beilstein J. Org. Chem. 2025, 21, 2548–2552, doi:10.3762/bjoc.21.197

• and Et3SiH as the hydrogen source [22], affording this natural product in 58% isolated yield. NMR data of the synthetic sample were found to be in agreement with those of previous literature (Tables S1 and S2, Supporting Information File 1). Moreover, the newly synthesized (+)-aglacin B (2) formed

Further elaboration of the stereodivergent approach to chaetominine-type alkaloids: synthesis of the reported structures of aspera chaetominines A and B and revised structure of aspera chaetominine B

• Jin-Fang Lü,
• Jiang-Feng Wu,
• Jian-Liang Ye and
• Pei-Qiang Huang

Beilstein J. Org. Chem. 2025, 21, 2072–2081, doi:10.3762/bjoc.21.162

• chaetominine A (12) and monocyclization product 26 in 31% and 45% yield, respectively. The spectral (1H and 13C NMR) data of our synthetic compound are different from those reported for the natural aspera chaetominine A, suggesting that the originally proposed stereochemistry for aspera chaetominine A (12) was

• chaetominine B (13) and monocyclization product 29 in 22% and 30% yield, respectively (Scheme 5). Once again, a comparison of the 1H and 13C NMR data of our synthetic compound 13 with those of the natural aspera chaetominine B showed that two compounds are different, indicating a misassignment of the structure

• (13) for aspera chaetominine B. To our delight, one-pot catalytic debenzylation–lactamization of 29 afforded lactamization product (–)-isochaetominine C (6). The 1H and 13C NMR data of compound 6 matched those of natural aspera chaetominine B suggesting that aspera chaetominine B is

Enantioselective desymmetrization strategy of prochiral 1,3-diols in natural product synthesis

• Lihua Wei,
• Rui Yang,
• Zhifeng Shi and
• Zhiqiang Ma

Beilstein J. Org. Chem. 2025, 21, 1932–1963, doi:10.3762/bjoc.21.151

• confirmed by X-ray crystallographic analysis. Comparative analysis of the 1H NMR data with authentic samples of the natural heliannuol G and heliannuol H enabled structural revision of these compounds, correcting prior misassignments in the literature [31][32]. Through enzyme-catalyzed asymmetric

Synthesis, biological and electrochemical evaluation of glycidyl esters of phosphorus acids as potential anticancer drugs

• Almaz A. Zagidullin,
• Emil R. Bulatov,
• Mikhail N. Khrizanforov,
• Damir R. Davletshin,
• Elvina M. Gilyazova,
• Ivan A. Strelkov and
• Vasily A. Miluykov

Beilstein J. Org. Chem. 2025, 21, 1909–1916, doi:10.3762/bjoc.21.148

• 2.41–3.24 ppm and the POCH2- fragment at 3.66–4.36 ppm can be observed. The NMR data for the glycidyl esters of phosphorus acids 1–3 are comparable to those of related compounds. Biological activity of glycidyl esters of phosphorus acids To evaluate the biological activity of diastereomeric mixtures of

• , 13C 100.6 MHz). 1H and 13C NMR data are reported with reference to solvent resonances, and 31P NMR spectra were reported with respect to external 85% H3PO4 (0 ppm). All experiments were carried out using standard Bruker pulse programs. Infrared (IR) spectra were recorded on a Bruker Vector-22

Preparation of spirocyclic oxindoles by cyclisation of an oxime to a nitrone and dipolar cycloaddition

• Beth L. Ritchie,
• Alexandra Longcake and
• Iain Coldham

Beilstein J. Org. Chem. 2025, 21, 1890–1896, doi:10.3762/bjoc.21.146

• /z): [M + H]+ calcd for C20H22NO4S, 372.1270; found: 372.1281; 1H NMR data as reported [30]. Ozone was bubbled through a solution of 3 (1.30 g, 3.74 mmol) in CH2Cl2 (22 mL) and MeOH (22 mL) at −78 °C. After 1 h, excess ozone was removed by bubbling argon gas through the solution. After 5 min

• , 124.0, 123.7, 108.4, 72.0, 48.4, 46.2, 26.4, 21.5; NMR data as reported (no lit. mp) [30]. Cycloadditions with the aldehyde 4 Aldehyde 4 (500 mg, 1.44 mmol), hydroxylamine hydrochloride (160 mg, 2.30 mmol), and iPr2NEt (0.48 mL, 2.76 mmol) in PhMe (10 mL) were heated to 60 °C. After 2 h, N

[3 + 2] Cycloaddition of thioformylium methylide with various arylidene-azolones in the synthesis of 7-thia-3-azaspiro[4.4]nonan-4-ones

• Daniil I. Rudik,
• Irina V. Tiushina,
• Anatoly I. Sokolov,
• Alexander Yu. Smirnov,
• Alexander R. Romanenko,
• Alexander A. Korlyukov,
• Andrey A. Mikhaylov and
• Mikhail S. Baranov

Beilstein J. Org. Chem. 2025, 21, 1791–1798, doi:10.3762/bjoc.21.141

• , with only trace amounts (or none) of the alternative form (dr >19:1). Moreover, comparison of NMR data within each series of heterocycles allowed us to reliably assert that the same isomer was observed in each specific group of substances. However, NMR data alone could not unambiguously assign the

Influence of the cation in hypophosphite-mediated catalyst-free reductive amination

• Natalia Lebedeva,
• Fedor Kliuev,
• Olesya Zvereva,
• Klim Biriukov,
• Evgeniya Podyacheva,
• Maria Godovikova,
• Oleg I. Afanasyev and
• Denis Chusov

Beilstein J. Org. Chem. 2025, 21, 1661–1670, doi:10.3762/bjoc.21.130

• ). The NMR data were collected using the equipment of the Center for molecular composition studies of INEOS RAS with financial support from the Ministry of Science and Higher Education of the Russian Federation (Contract No. 075-00276-25-00).

Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent Cyrene^TM under one-pot conditions

• Zoltán Medgyesi and
• László T. Mika

Beilstein J. Org. Chem. 2025, 21, 1544–1551, doi:10.3762/bjoc.21.117

• = 6.3 Hz, 1H, CH), 2.73–2.02 (m, 4H, CH2); 13C NMR (75 MHz, CDCl3, TMS) δ 200.3 (CO), 101.5 (CH), 73.1 (CH), 67.6 (CH2), 31.1 (CH2), 29.9 (CH2). The NMR data correspond to the published results. Methyl 4-methoxyvalerate and ethyl 4-ethoxyvalerate were prepared using the published method [47]. The

Highly distinguishable isomeric states of a tripodal arylazopyrazole derivative on graphite through electron/hole-induced switching at ambient conditions

• Himani Malik,
• Sudha Devi,
• Debapriya Gupta,
• Ankit Kumar Gaur,
• Sugumar Venkataramani and
• Thiruvancheril G. Gopakumar

Beilstein J. Org. Chem. 2025, 21, 1496–1507, doi:10.3762/bjoc.21.112

• (≈120°), the angle between the vectors. The intermolecular distance obtained from STM corresponds to the lateral length of the EEE isomer (F to F distance is 22.06 Å). Thus, we conclude that the adlayer is formed by the energetically most favorable EEE isomer. This is also consistent with the NMR data

Wittig reaction of cyclobisbiphenylenecarbonyl

• Taito Moribe,
• Junichiro Hirano,
• Hideaki Takano,
• Hiroshi Shinokubo and
• Norihito Fukui

Beilstein J. Org. Chem. 2025, 21, 1454–1461, doi:10.3762/bjoc.21.107

• temperature. These are attributable to the mixture of conformers with the figure-eight conformation as minor and the bathtub conformation as major conformer with a ratio of ca. 1:7. The obtained temperature-dependent 1H NMR data were subjected to the van't Hoff plot, affording an enthalpy ΔH and an entropy ΔS

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

• Supporting Information File 1, Figure S16) confirming that both of these protons were present on the same side of the double bond. The structure of 3 was confirmed using mass spectrometry, 1D and 2D NMR data as a new compound, named pseudomonin F. Compound 4 was isolated as a pink oil. The negative mode

• HRESIMS gave a prominent molecular ion at m/z 234.074 corresponding to C12H13NO4 (Δ: +1.2 ppm, calcd. for C12H12NO4, 234.0772) having 7 degrees of unsaturation. Detailed analysis of the 1H NMR data of 4 showed similar resonance signals observed in 3, however, an additional intense sharp singlet at δH 3.68

• configuration to that of 3, evidenced by a medium through space correlation between the amide proton, H-8 (δH 9.9) and the methyl, H3-12 (δH 1.76) in the NOESY spectrum (see Figure 2 and Supporting Information File 1, Figure S23). Based on HRESIMS, 1D and 2D NMR data, the structure of compound 4, was confirmed

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

• previous reports [10]. A single and identical product was obtained from each reaction and the product, 2, was characterised following analysis of HRESIMS and 1D (1H, 13C) and 2D (COSY, HSQC, HMBC, ROESY) NMR data. The HRESIMS data of 2 showed a Na adduct ion at m/z 372.0991 [M + Na]+ (calcd for

• MHz NMR spectrometer equipped with a cryoprobe. MestreNova™ version 14.3.3 software was used for NMR data analysis. The 1H and 13C NMR chemical shifts were referenced to solvent peaks for (CD3)2SO (δH 2.50, δC 39.52). LRESIMS data was recorded on a Thermo Scientific (Waltham, MA, USA) UltiMate™ 3000

Supramolecular assembly of hypervalent iodine macrocycles and alkali metals

• Krishna Pandey,
• Lucas X. Orton,
• Grayson Venus,
• Waseem A. Hussain,
• Toby Woods,
• Lichang Wang and
• Kyle N. Plunkett

Beilstein J. Org. Chem. 2025, 21, 1095–1103, doi:10.3762/bjoc.21.87

• fluctuation of the concentration of the host and the guest, which contribute to the x-axis in the fitting process. The isothermal fitting to 2:1 models is often prone to overfitting with NMR data and is noticeable with the fit for 1. However, the general trend does correlate with the strength of the

Studies on the syntheses of β-carboline alkaloids brevicarine and brevicolline

• Benedek Batizi,
• Patrik Pollák,
• András Dancsó,
• Péter Keglevich,
• Gyula Simig,
• Balázs Volk and
• Mátyás Milen

Beilstein J. Org. Chem. 2025, 21, 955–963, doi:10.3762/bjoc.21.79

• brevicarine (2, isolated as its dihydrochloride salt). Based on the above results, Eschweiler–Clarke methylation of primary amine 25 was applied for the synthesis of N-methylbrevicarine (27) [39], a close structural analogue of alkaloid 2. The NMR data of our synthesized brevicarine (2) base and

• publications [19][23][24] confirmed the structure with IR and MS data, or by reactivity. Herein, we report the full set of assigned 1H and 13C NMR data for both the base and the dihydrochloride salt. In the course of our efforts devoted to elaborating a new and efficient synthesis of brevicarine (2), we

• has been elaborated rendering the preparation of larger amounts of the target compound possible. NMR data of brevicarine base and dihydrochloride salt were fully assigned for a further confirmation of their structure. In the course of the unsuccessful attempts for a new synthesis of brevicolline, we

Data accessibility in the chemical sciences: an analysis of recent practice in organic chemistry journals

• Sally Bloodworth,
• Cerys Willoughby and
• Simon J. Coles

Beilstein J. Org. Chem. 2025, 21, 864–876, doi:10.3762/bjoc.21.70

• NMR data by some journals supports author compliance. We find that, although authors meet mandated requirements, there is very limited compliance with data sharing policies that are only recommended by journals. Overall, there is little evidence to suggest that authors’ publishing practice meets FAIR

• identifiers for all reported compounds. Keywords: data availability; FAIR principles; journal guidelines; NMR data; organic chemistry; Introduction Fundamental to science is the ability of researchers to build upon the findings of others. Scientific data are no longer perceived as simply an output of

• ’ deposition in open repositories, and are these data accessible and curated? Is there evidence to suggest that authors apply FAIR data guidance? Does the existence of specific recommendations for FAIR data practice in publishing NMR data by some journals encourage compliance? Finally, we discuss what the

Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities

• Rémy B. Teponno,
• Sara R. Noumeur and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48

• m/z 347.1098 [M + Na]+ and 671.2314 [2M + Na]+ corresponding to the molecular formula C16H20O7 (calcd. for C16H20O7Na+: 347.1101). The NMR data of compound 6 showed the presence of a trans-2-methyl-2-butenoyl moiety when compared to those of the parent compound [24]. This was revealed by proton

New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives

• Yuriy I. Horak,
• Roman Z. Lytvyn,
• Andrii R. Vakhula,
• Yuriy V. Homza,
• Nazariy T. Pokhodylo and
• Mykola D. Obushak

Beilstein J. Org. Chem. 2025, 21, 444–450, doi:10.3762/bjoc.21.31

• products were identified via NMR as 4,4a,5,6,7,7a-hexahydro-3aH-furo[2,3-f]isoindoles. The structures of compounds 5 were confirmed by NMR spectroscopy data (for details and discussion see Supporting Information File 1). The NMR data for the obtained furoindole skeleton signals and spin-coupling constants

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• supported by NMR data showing the formation of the respective intermediates. Previously, this stabilisation of a similar α-glycosyl intermediate had been successfully implemented by Crich et al. leading to high β-selectivity in challenging mannose and rhamnose moieties [37]. The moderate yield and β

Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

• Yurii A. Sayapin,
• Eugeny A. Gusakov,
• Inna O. Tupaeva,
• Alexander D. Dubonosov,
• Igor V. Dorogan,
• Valery V. Tkachev,
• Anna S. Goncharova,
• Gennady V. Shilov,
• Natalia S. Kuznetsova,
• Svetlana Y. Filippova,
• Tatyana A. Krasnikova,
• Yanis A. Boumber,
• Alexey Y. Maksimov,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

• large Stokes shift values (Table 2, Figure 5). This is consistent with the above conclusion about the existence of tautomeric equilibrium 7,8 (OH)–7,8 (NH) in solutions based on NMR data and DFT quantum chemical calculations (Scheme 2). The emission with a larger Stokes shift appears to correspond to

Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia

• Rita Toshe,
• Syeda J. Khalid,
• Blondelle Matio Kemkuignou,
• Esteban Charria-Girón,
• Paul Eckhardt,
• Birthe Sandargo,
• Kunlapat Nuchthien,
• J. Jennifer Luangsa-ard,
• Till Opatz,
• Hedda Schrey,
• Sherif S. Ebada and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23

• that it is a related derivative to two yellow pyridone pigments, farinosones A and B, that were previously reported from Cordyceps farinosa syn. Paecilomyces farinosus [8][9]. A detailed comparison of the 1H and 13C NMR data of 1 and farinosones A/B revealed that instead of a deshielded pyridone

• ), 300 (0.5), 265 (0.6) 218 (2.4); NMR data (1H: 500 MHz, 13C: 125 MHz, DMSO-d6) see Table 1; HRESIMS m/z: [M – H2O + H]+ calcd for C25H28NO4+, 406.2026; found, 406.2020; [M + H]+ calcd for C25H30NO5+, 424.2118; found, 424.2126; [M + Na]+ calcd for C25H29NNaO5+, 446.1962; found, 446.1947. Farinosone A (2

• ): Pale yellow amorphous solid; UV–vis (MeOH) λmax: 368, 224, 200 nm; NMR data (1H: 500 MHz, 13C: 125 MHz, acetone-d6) comparable to the previously described spectral data [8]; HRESIMS m/z: [M + H]+ calcd for C25H28NO4+, 406.2103; found, 406.2103. Farinosone B (3): Bright yellow powder; UV–vis (MeOH) λmax

Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina

• Shin-ichiro Kurimoto,
• Kouta Inoue,
• Taito Ohno and
• Takaaki Kubota

Beilstein J. Org. Chem. 2024, 20, 3215–3220, doi:10.3762/bjoc.20.267

• (partial structures a and b, respectively, in Figure 2), which were characteristic of psammaplysins, in ceratinadin G (1) was suggested by comparison of its 1H and 13C NMR data with those of known psammaplysin derivatives such as psammaplysins A and F (2) [4][5][6][10][11][12]. HMBC correlations (H-1/C-2

• 28138) and 258 (ε 10233); IR (film/KBr) νmax: 3337, 2935, 2878, 2849, 2234 (weak), 1671, 1624, 1595, 1542, 1457, 1257, 1199, 1145, 1119, 1046, 954, 898, 738 cm−1; ECD (MeOH) λmax, nm: 211 (Δε −15.84), 239 (Δε 7.99), 281 (Δε 0.07); 1H and 13C NMR data (Table 1); HRESIMS (m/z): [M + Na]+ calcd for

• of ceratinadin G (1) and psammaplysin F (2). Selected 2D NMR correlations for ceratinadin G (1). ECD spectra of ceratinadin G (1) and psammaplysin F (2) in MeOH. 1H and 13C NMR data of ceratinadin G (1) in methanol-d4. Supporting Information Supporting Information File 46: 1H NMR, 13C NMR, 1H-1H

Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• C17H22Br2N2O4. Ianthelliformisamine F (6) was isolated as a stable brown gum. The LRESIMS of 6 indicated the presence of two bromine atoms due to a 1:2:1 ion cluster at m/z 334/336/338 [M + H]+, whilst the HRESIMS data enabled a molecular formula of C10H9Br2NO2 to be assigned. Comparison of the 1D NMR data of 6

• commercially available primary amine, 1-(3-aminopropyl)pyrrolidin-2-one completed the total synthesis of the natural product in an overall yield of 1.5%. The NMR data comparison of the natural product and our synthetic compound was essentially identical. Due to our interest in the identification of potential

• sufficient quantities of the minor natural products for characterisation and biological assessment with similar recoveries obtained. Ianthelliformisamine D (4): Stable brown gum; UV (MeOH) λmax, nm (log ε): 226 (4.01), 278 (3.86); 1H and 13C NMR data (DMSO-d6), see Table 1; LRESIMS (m/z): 459/461/463 [M + H

The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis

• Jonas Holste,
• Paul Weldon,
• Donald Boyer and
• Stefan Schulz

Beilstein J. Org. Chem. 2024, 20, 2644–2654, doi:10.3762/bjoc.20.222

• pentane and diethyl ether (100:2) and obtained as a 1:1 mixture of diastereomers. This was followed by silver nitrate column chromatography using pentane and ethyl acetate (97.5:2.5) to enrich one diastereomer (de(E) = 50%). The NMR data were in agreement with published values [31]. Colorless oil: 15 mg

Synthesis and cytotoxicity studies of novel N-arylbenzo[h]quinazolin-2-amines

• Battini Veeraiah,
• Kishore Ramineni,
• Dabbugoddu Brahmaiah,
• Nangunoori Sampath Kumar,
• Hélène Solhi,
• Rémy Le Guevel,
• Chada Raji Reddy,
• Frédéric Justaud and
• René Grée

Beilstein J. Org. Chem. 2024, 20, 2592–2598, doi:10.3762/bjoc.20.218

• reduced pressure to afford crude compound 2 as pale-yellow solid (65% yield). Its NMR data are in agreement with literature [5]. 1H NMR (400 MHz, DMSO-d6, δ ppm) 10.49 (s, 1H), 8.26 (d, J = 8.4 Hz, 1H), 8.10 (d, J = 8.0 Hz, 1H), 7.90 (d, J = 8.8 Hz, 1H), 7.84–7.74 (m, 3H). Step 2: Synthesis of benzo[h

Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols

• Smaher E. Butt,
• Konrad Kepski,
• Jean-Marc Sotiropoulos and
• Wesley J. Moran

Beilstein J. Org. Chem. 2024, 20, 2455–2460, doi:10.3762/bjoc.20.209

• benzoyl group on the nitrogen atom preventing equilibration to the thermodynamic piperidine product [21]. Basic workup hydrolyzes the trifluoroacetoxy ester in 14 to alcohol 7a. Consideration of the literature NMR data for the three possible isomeric products (i.e., pyrrolidine, piperidine, and