Total syntheses of highly oxidative Ryania diterpenoids facilitated by innovations in synthetic strategies

• Zhi-Qi Cao,
• Jin-Bao Qiao and
• Yu-Ming Zhao

Beilstein J. Org. Chem. 2025, 21, 2553–2570, doi:10.3762/bjoc.21.198

• natural product. Similarly, starting from 57, installation of an allyl group at C2, followed by oxidative cleavage, reduction, and deprotection, provided cinncassiol B (7). Subjecting this compound to an acid-promoted fragmentation reaction then completed the total synthesis of cinncassiol A (9

• route commenced from (−)-pulegone. After introducing oxidation states at C6 and C10 and installing an alkynyl group at C11, oxidative cleavage of a double bond yielded the key propargylic alcohol intermediate 66. This compound underwent a 1,2-addition with alkynyl Grignard reagent 67, and the resulting

Transformation of the cyclohexane ring to the cyclopentane fragment of biologically active compounds

• Natalya Akhmetdinova,
• Ilgiz Biktagirov and
• Liliya Kh. Faizullina

Beilstein J. Org. Chem. 2025, 21, 2416–2446, doi:10.3762/bjoc.21.185

• (III) and iodine(III), and Wolff rearrangement. 2.1 Benzilic acid and semipinacol-type rearrangements The strategy of ring contraction using the benzilic acid-type rearrangement was used by Zhang et al. [38] for the asymmetric synthesis of 4β-acetoxyprobotryane-9β,15α-diol (52). This compound contains

• methylcyclopentanone 238 with a yield of 26%. This compound can be used in the synthesis of isoboonein (239) [104]. In compound 146, the effect of the keto group is more significant than that of the dioxolane fragment, as is known for this type of compounds. Therefore, changes to this functionality or its removal can

The high potential of methyl laurate as a recyclable competitor to conventional toxic solvents in [3 + 2] cycloaddition reactions

• Ayhan Yıldırım and
• Mustafa Göker

Beilstein J. Org. Chem. 2025, 21, 2389–2415, doi:10.3762/bjoc.21.184

• functional solvent(s) of our solute icon in this tool and following the update, the parameter values given above for the relevant nitrone were readily obtained. As can be seen from the figure, methyl laurate is a good alternative to competing toxic organic solvents that are good solvents for this compound

Synthetic study toward vibralactone

• Liang Shi,
• Jiayi Song,
• Yiqing Li,
• Jia-Chen Li,
• Shuqi Li,
• Li Ren,
• Zhi-Yun Liu and
• Hong-Dong Hao

Beilstein J. Org. Chem. 2025, 21, 2376–2382, doi:10.3762/bjoc.21.182

• -lactone with an all-carbon quaternary center and two trisubstituted olefin moieties. It is therefore not surprising that this compound has attracted considerable interest from both the chemical biology and synthetic chemistry communities. Sieber and co-workers disclosed that vibralactone can target ClpP1

Recent advances in Norrish–Yang cyclization and dicarbonyl photoredox reactions for natural product synthesis

• Peng-Xi Luo,
• Jin-Xuan Yang,
• Shao-Min Fu and
• Bo Liu

Beilstein J. Org. Chem. 2025, 21, 2315–2333, doi:10.3762/bjoc.21.177

• [20]. This compound significantly elevates reactive oxygen species levels in murine peritoneal macrophages (73 ± 12%) and exhibits potential as a lead for developing immunomodulatory agents. In 2021, Yang’s group reported a concise enantioselective total synthesis of (+)-cyclobutastellettolide B

Research towards selective inhibition of the CLK3 kinase

• Vinay Kumar Singh,
• Frédéric Justaud,
• Dabbugoddu Brahmaiah,
• Nangunoori Sampath Kumar,
• Blandine Baratte,
• Thomas Robert,
• Stéphane Bach,
• Chada Raji Reddy,
• Nicolas Levoin and
• René L. Grée

Beilstein J. Org. Chem. 2025, 21, 2250–2259, doi:10.3762/bjoc.21.172

• been able to transform this compound into a derivative having a significant affinity toward this kinase (VS-77, IC50 = 0.3 μM). Further, this compound has kept good activities against the other CLKs, and therefore can be qualified as a new pan-inhibitor of the CLKs. Unexpectedly, this modification has

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

• -10, previously known as ent-11-epi-chaetominine) in 32% yield starting from ʟ-Trp and ʟ-Ala [64]. In the last step of that total synthesis, the diastereomeric monocyclization product 22 was obtained as the major product (48% yield). Exposing this compound to an aged K2CO3/MeOH solution at 35 °C for

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

• %) and BzO− (43%), additional signals consistent with the O-benzoylated species 3 were identified. This compound was synthesized independently from benzoyl chloride and 1-methylimidazole (see Supporting Information File 1) with spiking of the crude 1H NMR spectrum with the authentic sample confirming the

Convenient alternative synthesis of the Malassezia-derived virulence factor malassezione and related compounds

• Karu Ramesh and
• Stephen L. Bearne

Beilstein J. Org. Chem. 2025, 21, 1730–1736, doi:10.3762/bjoc.21.135

• debenzylated by Pd-catalyzed hydogenation to cleanly yield 25c. This affords a route to such compounds bearing hydroxylated aromatic groups that employs milder conditions than previously reported [22][24]. Finally, we prepared N,N′-dibenzylmalassezione (25d). Initially, this compound was prepared with the

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

• of the resulting products in developing chiral organocatalysts was investigated as well. For instance, 28a was converted to a thiourea-tertiary amine 29 through a four-step procedure in an overall 36% yield. This compound was then utilized as the catalyst in the electrophilic amination reaction

3-Aryl-2H-azirines as annulation reagents in the Ni(II)-catalyzed synthesis of 1H-benzo[4,5]thieno[3,2-b]pyrroles

• Julia I. Pavlenko,
• Pavel A. Sakharov,
• Anastasiya V. Agafonova,
• Derenik A. Isadzhanyan,
• Alexander F. Khlebnikov and
• Mikhail S. Novikov

Beilstein J. Org. Chem. 2025, 21, 1595–1602, doi:10.3762/bjoc.21.123

• the NHC-complex, IPrCuCl, the formation of cycloadduct 11 was detected, which was isolated in 10% yield (Scheme 6). The formation of this compound implies the cleavage of the azirine N−C2 bond, indicating that the IPrCuCl-catalyzed reaction proceeds by a different mechanism, likely involving the

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

• triethylamine hydrochloride. This method has proven to be simple and effective in most cases, with the exception of compound 5g. The moderate solubility of this compound in diethyl ether led to partial precipitation from the reaction mixture. It is worth noting that chromatographic purification is also possible

• , was observed for the spiro-compound 5l, which contains a p-nitro group in the aromatic core of the nitrile oxide fragment. This compound was obtained in excellent yield of 93% and 88% using the dropwise and diffusion mixing technique, respectively. This result may be explained by the optimal

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

• (mp 136‒138 °C) in high yield of 86%. The 13C NMR spectrum registered for this compound revealed a shift of the S‒C‒S atom, incorporated into the cyclobutanone ring, at 74.8 ppm. On the other hand, the thioaminal functionality with N‒C‒S moiety located within the tetrazole ring, shows a signal at

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

• , while compound 68e emits blue light (ΦF = 0.37) and demonstrates pronounced AIE in the solid state. Concurrently, Jiang’s group reported 69b, the first hetero[4]helicene-type molecule exhibiting both CPL and TADF [83]. This compound displays a high ΦF of 0.51 and a |glum| of 1.2 × 10−3. OLED devices

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

• OH functionality in compound 2 gives possibility to influence the tautomerism in this compound dynamically by protonation/deprotonation. The tautomeric and switching properties of compounds 1 and 2 have been revealed by using quantum-chemical calculations, UV–vis and NMR spectroscopy and UV

• ][87][88]. Obviously, in the case of compound 2 the relaxation back to the ground state through the CI in the N=N bond isomerization region, which is the only option in this compound to return back to the ground state, populates exclusively the ground state E instead of Ecis. Is there a potential for

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

• applications, the research group has also developed two practical and scalable syntheses of this compound: one based on oxidation of 3-oxetanol (130) (obtained from epichlorohydrin), and the other on a Williamson etherification of dihydroxyacetone (129) [10][11][12]. In 2010, Zhang et al. added another

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

• demonstrated the homolytic cleavage of the N–O bond using N-(tert-butyl)-O-(1-phenylvinyl)-phenylhydroxyamide as a HAT reagent [78][79]. This compound was capable of initiating the formation of amidyl radicals through visible light activation. Although their controlled experiments showed that this method was

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

• % yield over three steps. This compound was isolated in its pure form as a white solid after recrystallization from ethanol, confirmed by HPLC and NMR. In parallel, the primary alcohol group of ent-38 was protected as a TBDMS ether, and the acetate group was converted to a tosyl ester by hydrolyzing the

• acetate functionality using potassium carbonate in methanol, followed by reaction with tosyl chloride in pyridine and DMAP. The product, ent-43, was obtained in 79.5% yield over three steps. This compound was reduced using LiAlH4 and treated with TBAF to remove the TBDMS group, yielding alcohol ent-40 in

• the late stage coupling with 137 was prepared from the known lactone 138 (Scheme 21). Following a literature procedure, compound 139 was obtained from lactone 138 and subsequently treated with CrO3 to yield ketone 140 in 90% yield [55]. The ketone moiety of this compound was then reacted with a Wittig

On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals

• Daniel Straub,
• Markus Gross,
• Mona E. Arnold,
• Julia Zolg and
• Alexander J. C. Kuehne

Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80

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

• ) were also ineffective. Based on literature data [42][43], we attempted the selective reduction of the pyrrole ring of compound 30 with NaCNBH3 in TFA as well. Surprisingly, trifluoroethylated product 32 was isolated. The formation of this compound can also be explained on the basis of analogies

Study of tribenzo[b,d,f]azepine as donor in D–A photocatalysts

• Katy Medrano-Uribe,
• Jorge Humbrías-Martín and
• Luca Dell’Amico

Beilstein J. Org. Chem. 2025, 21, 935–944, doi:10.3762/bjoc.21.76

• electron-withdrawing group [31]. Additionally, it is possible that the mobility of core 4 contributes to this behavior, as evidenced by the observation that the DE is not present in the more rigid structures 5a and 6a. In this compound, we did not observe changes in the absorption profile during the

Recent advances in the electrochemical synthesis of organophosphorus compounds

• Babak Kaboudin,
• Milad Behroozi,
• Sepideh Sadighi and
• Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex

• Maurizio Iannuzzi,
• Thomas Hohmann,
• Michael Dyrks,
• Kilian Haoues,
• Katarzyna Salamon-Krokosz and
• Beate Koksch

Beilstein J. Org. Chem. 2025, 21, 659–669, doi:10.3762/bjoc.21.52

• configuration was determined by analyzing the 1H NMR spectrum in the δ = 2.8–1.7 ppm region, which displayed the characteristic diastereotopic hydrogen atoms of this compound, as previously reported by Biava et al. [15]. Unfortunately, the corresponding (2S,4S)-isomer 12b was intractable for isolation (yield

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

• -carbonyl group was linked through an ester bond and the only hydroxy group available for this esterification was the one at C-7. This compound was finally elucidated as massarilactone D 3,4-di-O-methacryloyl-7-O-(6-chloro-3,4-dihydro-2,5-dimethyl-2H-pyran-2-carbonyl). For the formation of compound 2, an

Formaldehyde surrogates in multicomponent reactions

• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

• which, after MMS formation, this reactive species is subsequently captured by the stabilized Cu(II) enolate of the ketone, to provide an α,β-unsaturated ketone intermediate F. This compound condenses with the aniline component to give an imine G that follows a cyclization and aromatization cascade