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Search for "alcohol" in Full Text gives 1171 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Thiadiazino-indole, thiadiazino-carbazole and benzothiadiazino-carbazole dioxides: synthesis, physicochemical and early ADME characterization of representatives of new tri-, tetra- and pentacyclic ring systems and their intermediates

  • Gyöngyvér Pusztai,
  • László Poszávácz,
  • Anna Vincze,
  • András Marton,
  • Ahmed Qasim Abdulhussein,
  • Judit Halász,
  • András Dancsó,
  • Gyula Simig,
  • György Tibor Balogh and
  • Balázs Volk

Beilstein J. Org. Chem. 2025, 21, 2220–2233, doi:10.3762/bjoc.21.169

Graphical Abstract
  • water (5 mL) was added. The mixture was extracted with EtOAc (3 × 5 mL), washed with water (5 mL) and brine (5 mL), dried over MgSO4 and evaporated to give crude products 3 or 10, which were purified by recrystallization from isopropyl alcohol or by flash chromatography. Method B for the preparation of
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Published 21 Oct 2025

Electrochemical cyclization of alkynes to construct five-membered nitrogen-heterocyclic rings

  • Lifen Peng,
  • Ting Wang,
  • Zhiwen Yuan,
  • Bin Li,
  • Zilong Tang,
  • Xirong Liu,
  • Hui Li,
  • Guofang Jiang,
  • Chunling Zeng,
  • Henry N. C. Wong and
  • Xiao-Shui Peng

Beilstein J. Org. Chem. 2025, 21, 2173–2201, doi:10.3762/bjoc.21.166

Graphical Abstract
  • copper catalyst was still required in that procedure. In 2023, Bera presented an electrochemical oxidative [3 + 2] cycloaddition of secondary propargyl alcohol to access 1,2,3-triazole (Scheme 19) [273]. After probing the reaction systematically, the optimal conditions were presented as following: a
  • mixture of propargyl alcohol 50 (0.7 mmol), NaN3 (2.8 mmol), n-Bu4NI (0.5 mmol) and MeCN (10 mL) under electrolysis (graphite rod as anode, stainless-steel plate as cathode, 11 mA) at rt for 10 h. According to the experimental results and density functional theory (DFT) calculations, a plausible mechanism
  • electrochemical annulation of alkynes with enamides. Electrochemical [3 + 2] cyclization of heteroarylamine was an efficient access towards imidazopyridine. The electrochemical oxidative [3 + 2] cycloaddition of secondary propargyl alcohol produced 1,2,3-triazole. In most of these above reactions, the target
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Published 16 Oct 2025

C2 to C6 biobased carbonyl platforms for fine chemistry

  • Jingjing Jiang,
  • Muhammad Noman Haider Tariq,
  • Florence Popowycz,
  • Yanlong Gu and
  • Yves Queneau

Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165

Graphical Abstract
  • electrocatalyst supported on nitrogen-doped carbon nanosheets (Cu/NCNSs). This catalyst exhibits high activity for the oxidation of various substrates, including GLY, gluconic acid (GLU), 5-hydroxymethylfurfural (HMF), benzyl alcohol (BA), furfuryl alcohol (FA), and ethylene glycol (EG) (Scheme 7) [35]. Park et
  • hydrogenation to produce furfuryl alcohol. This latter is a versatile intermediate for the production of resins, coatings, polymers and used as a solvent. It can also be converted into other chemicals through oxidative cleavage, over-reduction and etherification (Scheme 49) [177]. Zhang et al. reported the use
  • Meerwein–Ponndorf–Verley reduction, while acetaldehyde is generated in situ by ethanol oxidation (Scheme 50). The equilibrium allows furfural to be simultaneously converted into furfuryl alcohol and 3-(2-furyl)acrolein in one pot through a redox reaction. The highest mass conversion rate of furfural can
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Published 15 Oct 2025
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  • reduction of diketone 28 for preparing alcohol 30 under the CBS conditions [8] with (S)-29 as the catalyst (Scheme 1) [14]. Notably, this reaction could be performed on multiple gram scales with satisfactory yield (72%) and ee value (92%). Protection of the alcohol group in 30 with TBSCl followed by
  • modification of the terminal double bond afforded ketoaldehyde 31. The 2-bromoallylation [15] of 31 with boronic ester 32 stereoselectively constructed the C3–OH group to give homoallylic alcohol 33. Next, a successive manipulation by removal of TBS group, CSA-catalyzed ketalization, and DMP oxidation of the
  • secondary alcohol to a ketone allowed for rapid construction of bicyclic ketone 34 in high overall yield. The oxidative dehydrogenation of 34 gave α,β-unsaturated bicyclic ketone 35 smoothly. Sequential A-ring construction and functional group modifications of 35 produced the diketone 36. Subsequently, 36
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Published 14 Oct 2025

Bioinspired total syntheses of natural products: a personal adventure

  • Zhengyi Qin,
  • Yuting Yang,
  • Nuran Yan,
  • Xinyu Liang,
  • Zhiyu Zhang,
  • Yaxuan Duan,
  • Huilin Li and
  • Xuegong She

Beilstein J. Org. Chem. 2025, 21, 2048–2061, doi:10.3762/bjoc.21.160

Graphical Abstract
  • propose the biosynthetic pathway, which has not yet been reported in Duh’s isolation report (Scheme 1a). In our proposal, the linear sesquiterpenoid trans-nerolidol (1) with a chiral tertiary alcohol undergoes dihydroxylation to generate triol 2, which further proceeds a C–C bond cleavage to afford
  • aldehyde 3. This linear aldehyde would be activated by an acid to trigger a key Prins cyclization with the trisubstituted olefin through reaction model 3 and generate a putative tertiary carbocation to be trapped by the chiral alcohol, providing bicycle 4 stereoselectively. Finally, the last olefin would
  • TBS protection in one pot. Oxidation of the primary alcohol using Swern oxidation gave the hydroxy aldehyde 3, which was activated with a formal silicon cation to trigger the Prins cyclization terminated by the tertiary alcohol, affording silylated bicycle 9 directly through the designed bioinspired
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Published 09 Oct 2025

Aryl iodane-induced cascade arylation–1,2-silyl shift–heterocyclization of propargylsilanes under copper catalysis

  • Rasma Kroņkalne,
  • Rūdolfs Beļaunieks,
  • Armands Sebris,
  • Anatoly Mishnev and
  • Māris Turks

Beilstein J. Org. Chem. 2025, 21, 1984–1994, doi:10.3762/bjoc.21.154

Graphical Abstract
  • using the symmetrical dithiophen-2-yliodonium p-tosylate (I-7). It should be noted that all products 8 were obtained with exclusive (E)-selectivity. Tetrahydrofuran 8a and some analogous compounds could be synthesized previously from alcohol 7d, but in two steps, employing a halogen electrophile-induced
  • described by us recently, among other possible transformations [21][22]. Interestingly, the addition of O-nucleophiles to form 1,3-carbofunctionalization products, can only be achieved in an intramolecular fashion. In the presence of an excess (5 equiv) of external an O-nucleophile R–OX (alcohol, carboxylic
  • internal nucleophiles (Scheme 4), that could be used instead of the alcohol. The carboxylic acid-containing silane 7 (R = COOH), which was obtained by stepwise oxidation of the alcohol 7d, failed to give the desired lactone 8t product due to O-arylation of the carboxylic acid, leading to phenyl alkyl ester
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Published 26 Sep 2025

Photochemical reduction of acylimidazolium salts

  • Michael Jakob,
  • Nick Bechler,
  • Hassan Abdelwahab,
  • Fabian Weber,
  • Janos Wasternack,
  • Leonardo Kleebauer,
  • Jan P. Götze and
  • Matthew N. Hopkinson

Beilstein J. Org. Chem. 2025, 21, 1973–1983, doi:10.3762/bjoc.21.153

Graphical Abstract
  • synthesis with complete reduction to the alcohol followed by partial re-oxidation often being conducted. Conclusion In conclusion, we have developed novel light-driven methodologies for the reduction of acylazolium salts using benzoylimidazolium triflate as a model substrate. In the presence of a
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Published 25 Sep 2025

Asymmetric total synthesis of tricyclic prostaglandin D2 metabolite methyl ester via oxidative radical cyclization

  • Miao Xiao,
  • Liuyang Pu,
  • Qiaoli Shang,
  • Lei Zhu and
  • Jun Huang

Beilstein J. Org. Chem. 2025, 21, 1964–1972, doi:10.3762/bjoc.21.152

Graphical Abstract
  • afforded the corresponding alcohol 18 in 89% yield with excellent enantioselectivity (98% ee) [25]. The hydroxy group in 18 was then protected via treatment with TBSCl in the presence of Et3N in CH2Cl2, yielding β-keto ester 15 in 52% yield. With diketone 15 in hand, we subsequently investigated the
  • of 21 with allyl alcohol and triphenylphosphine afforded transesterification product 22 in 21% yield [33], accompanied by unidentified decarboxylation by-products. A variety of standard conditions failed to promote the palladium-catalyzed decarboxylative allylation of allylic β-ketocarboxylate
  • controlled by the stereoelectronic effect of the axial hydroxy group at C11 (Scheme 4) [28]. First, β-keto ester 21 was synthesized (Scheme 5). Cross-metathesis of allylic alcohol 18 and olefin 28 with the assistance of the Hoveyda–Grubbs second-generation catalyst delivered the desired product 27 in 68
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Published 24 Sep 2025

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

Graphical Abstract
  • intramolecular cyclization of 16 generated benzofuran 17 in 83% yield. After protecting the phenolic hydroxy group of 17, cross-metathesis (CM) with allylic alcohol 18 catalyzed by 13 furnished intermediate 19. Desilylation of 19 produced heliannuol G (20) and heliannuol H (21), with the structure of 21
  • 25 with vinyl butanoate and PPL delivered monoester 26 in 92% yield (99% ee). The axial chirality was transferred to the C7’ stereocenter through a Ag(I)-catalyzed cycloisomerization of the allenol, constructing the dihydrofuran ring. Lipase-catalyzed ester hydrolysis provided allylic alcohol 27
  • . Alcohol 28 was obtained from 27 in two steps, and was subsequently converted to hyperione A (30) and ent-hyperione B (31) by refluxing in toluene with Shvo’s catalyst 29. Notably, the authors found that hyperione A (30) could be obtained in higher yield and enantiopurity from alcohol 28 via a two-step
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Published 18 Sep 2025

Rhodium-catalysed connective synthesis of diverse reactive probes bearing S(VI) electrophilic warheads

  • Scott Rice,
  • Julian Chesti,
  • William R. T. Mosedale,
  • Megan H. Wright,
  • Stephen P. Marsden,
  • Terry K. Smith and
  • Adam Nelson

Beilstein J. Org. Chem. 2025, 21, 1924–1931, doi:10.3762/bjoc.21.150

Graphical Abstract
  • estimation of the yield of each product (Figure 2, panel B). It was found that many reactions involving alcohol- (e.g., C1–5, C8, C11 and C14) and indole- (e.g., C3, C12 and C15) containing co-substrates yielded intermolecular products, whilst those involving nitrile-containing co-substrates (C9 and 10) and
  • reaction modes of dirhodium carbenoids that were possible [14]. Overall, products were formed via O–H insertion into an alcohol (to give 14 products) or phenol (→ 2-4 and 3-4a); N–H insertion into an indole (→ 1-3a, 1-15b, 2-3a, 2-15b and 4-3), sulfonamide (→ 2-6), aminopyrimidine (→ 2-13 and 4-13) or
  • were obtained. In the case of co-substrate 3, which contains both an indole and an alcohol, thus raising chemoselectivity issues, products were observed from both O–H and N–H insertion. It is notable, however, that despite many of the co-substrates having multiple potentially reactive sites, one
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Published 17 Sep 2025

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

Graphical Abstract
  • -dipole, access to 1,3-amino-alcohol functionality is possible. This arrangement is present in many Alstonia alkaloids, and we envisaged using this cycloaddition chemistry to set up the bridged amine ring system found in these natural products. Bridged and spirocyclic ring systems are known to be
  • the presence of a Lewis acid. The use of BF3·OEt2 gave a low yield of the desired alcohol 2 [29]. This was improved slightly with Sc(OTf)3 as the Lewis acid, which could be used substoichiometrically [30]. The alcohol 2 was converted to the tosylate 3 and subsequent ozonolysis gave the aldehyde 4. The
  • ), dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/petrol 1:2, to give the alcohol 2 (824 mg, 30%) as an amorphous solid; data as reported [30]. Et3N (1.5 mL, 10.8 mmol) was added to the alcohol 2 (782 mg, 3.6 mmol), TsCl (1.03 g
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Published 11 Sep 2025

Preparation of a furfural-derived enantioenriched vinyloxazoline building block and exploring its reactivity

  • Madara Darzina,
  • Anna Lielpetere and
  • Aigars Jirgensons

Beilstein J. Org. Chem. 2025, 21, 1737–1741, doi:10.3762/bjoc.21.136

Graphical Abstract
  • applications to functional materials, pharmaceutically relevant compounds, and agrochemicals [8][9][10][11][12][13][14][15][16][17]. In our recent work, we have developed a Torii-type electrosynthesis of unsaturated esters 3a–c starting from furfural (1) and amino alcohol conjugates 2a–c [18]. The process
  • proposed mechanism of product 7 formation. Electrochemical oxidation of protected amino alcohol 2d to ester 3d. Supporting Information Supporting Information File 8: Experimental procedures, characterization data and copies of NMR spectra. Funding This project has received funding from the European
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Published 29 Aug 2025

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
  • 72% yield and excellent regio- and stereoselectivity. Regarding the acceptor, compound 6 harbored two free alcohol groups at the C3 and C2 positions. Since the C3 alcohol group is less sterically hindered and exhibits better nucleophilicity, the glycosidic bond formed regioselectively at the C3
  • position. Additionally, THF was used as a solvent to enhance the α-selectivity of the reaction [41][42][43]. Next, while both compounds 8 and 9 can act as acceptors, compound 9, a primary alcohol, exhibits greater nucleophilicity. Using the TolSCl/AgOTf promoter system at −70 °C, the β-linked disaccharide
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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
  • . Moreover, an axially chiral tertiary alcohol-phosphine 42 was prepared from 39a through a three-step procedure including N-methylation, reduction of phosphine oxide, and Grignard addition to ester. Subsequently, 42 was applied as a bifunctional Lewis base organocatalyst in the formal [4 + 2] cyclization
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Published 19 Aug 2025

Formal synthesis of a selective estrogen receptor modulator with tetrahydrofluorenone structure using [3 + 2 + 1] cycloaddition of yne-vinylcyclopropanes and CO

  • Jing Zhang,
  • Guanyu Zhang,
  • Hongxi Bai and
  • Zhi-Xiang Yu

Beilstein J. Org. Chem. 2025, 21, 1639–1644, doi:10.3762/bjoc.21.127

Graphical Abstract
  • compound [29] and can be prepared from readily available m-anisyl alcohol by using iodination and bromination reactions (see Supporting Information File 1 for the details). Subsequently, an SN2 reaction between 2 and tert-butyl cyclopropanecarboxylate (3) in the presence of LDA delivered product 4 in 87
  • % yield with a cyclopropyl group. Then reducing the carboxylate group in 4 with DIBAL-H afforded alcohol 5 in 67% yield. Next, Sonogashira coupling reaction between 5 and trimethylsilylacetylene generated 6 with an alkyne moiety quantitatively. After that, the hydroxy group in 6 was oxidized into a
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Published 14 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
  • TMSOTf at 0 °C to room temperature, successfully furnished the desired α-Man-(1→3)-α-Man-(1→3)-α-Man trisaccharide 10 in 87% yield in a one pot manner. Removal of TBDPS group in 10 with 70% HF·pyridine and subsequent phosphitylation of the resulting free alcohol with phosphoramidite 11 provided the
  • over the following steps: 1) deprotection of the TBDPS group, 2) phosphitylation of the free alcohol with phosphoramidite 11 in the presence of 1H-tetrazole and 4 Å MS, and 3) oxidation of the phosphite by mCPBA. Hydrogenolysis of Bn and Cbz groups in 14 with Pd(OH)2/C and subsequent saponification of
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Published 06 Aug 2025

Calcium waste as a catalyst in the transesterification for demanding esters: scalability perspective

  • Anton N. Potorochenko and
  • Konstantin S. Rodygin

Beilstein J. Org. Chem. 2025, 21, 1520–1527, doi:10.3762/bjoc.21.114

Graphical Abstract
  • ranging from 51% to 99%, depending on the alcohol and catalyst loading (1–10 wt %). Alcohols with additional functional groups were converted to the respective esters suitable for further modifications. The CS600 catalyst proved promising for the transesterification of low-molecular-weight esters, medium
  • , and minor components did not affect the reaction or were inert. Since the transesterification with a catalyst derived from carbide slag (CS600) and commercial (or obtained from another source) calcium oxide proceeds by the same mechanism with the formation of a new ester and an alcohol as byproduct
  • processing. Next, the CS600 catalyst was investigated in the transesterification of soybean oil with various alcohols. The overall results of the transesterification are presented in Scheme 1. All the reactions were carried out at the boiling point of the corresponding alcohol, using different CS600 loadings
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Published 28 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
  • protonate this basic fragment, undergo 1,3-addition leading to corresponding products of S,S-, O,S-, or N,S-acetal type. For example, trapping of the in situ-generated adamantanethione S-methanide (1a) with tert-butylthiol or benzyl alcohol leads to the corresponding S,S-dithioacetal and O,S-thioacetal
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Published 23 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

Graphical Abstract
  • form of catalysis from simple acids to metal catalysts [46]. Similar to the previous examples, the first step was the optimization of the conditions using the esterification of benzyl alcohol (12a) with acetic anhydride (8) and acetic acid (13), respectively. The optimization data are summarized in
  • ). Optimization of the high pressure-assisted catalyst- and additional solvent-free synthesis of acetylsalicylic acid (9). Optimization of the HHP-assisted catalyst-free esterification of benzyl alcohol (12a). Molecular volumes of the reactants and products and the reaction volume (ΔV) for the reaction of o
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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
  • with alcohol C–H functionalisation, thus creating a unique synthetic strategy towards oxetane formation that avoids tedious multistep substrate preparations (Scheme 7) [42]. It can be initiated from simple, unactivated primary or secondary alcohols, tolerates various functional groups such as acetals
  • chlorides (Scheme 11a) [44]. The authors found that the secondary alcohol precursors were less reactive and that best results were obtained at low temperature (≤−50 °C) and in chlorinated solvents. The synthesis of these cages was later revisited by Le Drian et al. in 2011 who studied a Lewis acid-catalysed
  • synthetic route to the repertoire which proceeds through a gold-catalysed oxidation of propargyl alcohol (131) [82]. Scheme 34 also shows selected transformations from the publications by Carreira et al. to provide a brief insight into what oxetane building blocks can be prepared from 3-oxetanone: these
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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

Graphical Abstract
  • . Dehydrogenation played a pivotal role as a key step also in the synthesis of larger π-scaffolds. For example, Murata and co-workers reported the synthesis of an azulene containing isomer of benzo[a]pyrene 9 (Scheme 2) [33]. Reduction of ketone 7 using LiAlH4 resulted in alcohol 8 which was subsequently
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Published 26 Jun 2025

Optimized synthesis of aroyl-S,N-ketene acetals by omission of solubilizing alcohol cosolvents

  • Julius Krenzer and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2025, 21, 1201–1206, doi:10.3762/bjoc.21.97

Graphical Abstract
  • -on of emission upon induced aggregation in alcohol–water mixtures [1]. This chromophore class has been extensively developed in recent years, even to aggregation-induced emissive (AIE) multichromophores [2] and even bichromophoric fluorimetric sensors [3][4]. The retrosynthesis of the title compounds
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Published 20 Jun 2025

Selective monoformylation of naphthalene-fused propellanes for methylene-alternating copolymers

  • Kenichi Kato,
  • Tatsuki Hiroi,
  • Seina Okada,
  • Shunsuke Ohtani and
  • Tomoki Ogoshi

Beilstein J. Org. Chem. 2025, 21, 1183–1191, doi:10.3762/bjoc.21.95

Graphical Abstract
  • % yield. Alcohol products, [4.3.3]_CH2OH and [3.3.3]_CH2OH, were then tested in acidic conditions using anhydrous FeCl3 as a Lewis acid. After the reactions, the alcohol proton signals at 1.54–1.58 ppm disappeared in the 1H NMR spectra, and aliphatic carbon ones at 63.1–63.2 ppm were largely up-field
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Published 18 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

Graphical Abstract
  • prepared via PMB removal of compound 21, which, in turn, was obtained through desulfonylation of compound 22. Compound 22 originated from the condensation of epoxide 23a with sulfone 26, which was produced by desilylation of 25 followed by converting the resulting primary alcohol into a sulfone group
  • LiAlH4 in ether to form alcohol 40 (89%) (Scheme 3). The primary alcohol 40 was then converted to its iodide derivative 42 (89%), from which single crystals were obtained, and its structure was determined unequivocally by XRD crystallography. Iodide 42 was then reacted with sodium phenylsulfinate in DMF
  • to afford the corresponding sulfone 41. However, Uguen found that a more efficient route involved treating alcohol 40 with tosyl chloride in pyridine and DMAP, followed by nucleophilic displacement with sodium thiophenol and oxidation of the resulting sulfide with m-CPBA, yielding sulfone 41 in 85
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Published 12 Jun 2025

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

  • Betty A. Kustiana,
  • Galuh Widiyarti and
  • Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

Graphical Abstract
  • with a catalytic base has also been applied to prepare cinnamate esters. For example, Heller and co-workers (2021) synthesized the ester 141 catalyzed by DBU which functioned as a Brønsted base for the alcohol (Scheme 43A) [81]. Impressively, the method could be scaled up to a multigram scale
  • with nucleophilic cinnamonitrile 149 to give benzocyclooctene 150 via iodonium intermediate 151 (Scheme 46) [86]. 2.2 Oxidative acylations Cinnamic ester or amide preparation could also be achieved by oxidizing cinnamyl alcohol, aldehyde, imine, and ketone as an alternative to the traditional O/N
  • -acylation of cinnamic acid above. 2.2.1 Alcohol oxidation: Kapdi and co-workers (2019) reported Pd-colloids-catalyzed esterification via Ag2O-catalyzed alcohol oxidation. Herein, cinnamyl alcohols were oxidized to the corresponding cinnamaldehydes catalyzed by Ag2O, followed by oxidative addition to Pd via
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Published 28 May 2025
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