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

• ]pyran-3(10bH)-one (4): UV (MeOH) lmax 250 nm; NMR data see Table 1 and Table 2; HRESIMS m/z: [M + H]+ calcd. for C18H23O5, 319.1540; found, 319.1542. Chemical synthesis of compounds 1-[5,7-Dihydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-8-yl]ethanone (5): A mixture of 2,4,6

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

• diffractometer. Nuclear magnetic resonance spectra were recorded on a JEOL ECX400 spectrometer. Glutaminase assays were measured on a Tecan Infinite M nano spectrophotometer. Reagents and solvents for chemical synthesis were used without additional purification. Chemical synthesis 3-Bromo-4

Concept-driven strategies in target-oriented synthesis

• David Yu-Kai Chen,
• Chao Li and
• Yefeng Tang

Beilstein J. Org. Chem. 2026, 22, 451–454, doi:10.3762/bjoc.22.32

• history of science. Indeed, organic compounds have an unparalleled track record in elucidating the mysteries behind a wide range of physical, chemical, and biological phenomena, and advances in chemical synthesis have been instrumental in these explorations. Specifically, target-oriented syntheses of

• of these research efforts is the identification of “feasible” and “efficient” synthetic pathways. As mentioned in the opening paragraph, as the field of target-oriented synthesis evolves beyond mere feasibility, approaching chemical synthesis solely from a “fast and furious” perspective may not truly

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

Total synthesis of asperdinones B, C, D, E and terezine D

• Ravi Devarajappa and
• Stephen Hanessian

Beilstein J. Org. Chem. 2025, 21, 2730–2738, doi:10.3762/bjoc.21.210

• bond formation and functional group compatibility presented unforeseen challenges. Methods for the chemical synthesis of prenyltryptophans (approach A, A–C) are scarce [25][26]. Adopting a bio-inspired approach, Ishikawa et al. treated tryptophan ethyl ester with prenyl alcohol in the presence of 2

Recent advancements in the synthesis of Veratrum alkaloids

• Morwenna Mögel,
• David Berger and
• Philipp Heretsch

Beilstein J. Org. Chem. 2025, 21, 2657–2693, doi:10.3762/bjoc.21.206

• dense stereochemistry and, thus, have stood long as benchmarks in chemical synthesis. Recently, these steroid alkaloids gained popularity as challenging targets in total synthesis, with a clear shift toward convergent strategies. Not only do these syntheses feature rapid assembly of their challenging

Recent advances in total synthesis of illisimonin A

• Juan Huang and
• Ming Yang

Beilstein J. Org. Chem. 2025, 21, 2571–2583, doi:10.3762/bjoc.21.199

• considerable interest from synthetic chemists. Although the intricate structures of this family have posed significant challenges to chemical synthesis, more than 30 total syntheses of Illicium sesquiterpenes have been reported until now [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22

Palladium-catalyzed regioselective C1-selective nitration of carbazoles

• Vikash Kumar,
• Jyothis Dharaniyedath,
• Aiswarya T P,
• Sk Ariyan,
• Chitrothu Venkatesh and
• Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2025, 21, 2479–2488, doi:10.3762/bjoc.21.190

• attention has been devoted to the chemical synthesis of carbazole and its derivatives [9][10][11][12][13][14]. To access substituted carbazole cores for pharmacophores and functional materials, two main synthetic routes are: i) sequential multistep syntheses of selectively substituted carbazoles and ii

The intramolecular stabilizing effects of O-benzoyl substituents as a driving force of the acid-promoted pyranoside-into-furanoside rearrangement

• Alexey G. Gerbst,
• Sofya P. Nikogosova,
• Darya A. Rastrepaeva,
• Dmitry A. Argunov,
• Vadim B. Krylov and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2025, 21, 2456–2464, doi:10.3762/bjoc.21.187

• .21.187 Abstract Furanoside derivatives are broadly present in the antigenic structures of pathogenic microorganisms and play a key role in their recognition by the host immune system. Despite the high demand for vaccine and diagnostic development, their chemical synthesis remains challenging. During the

A chiral LC–MS strategy for stereochemical assignment of natural products sharing a 3-methylpent-4-en-2-ol moiety in their terminal structures

• Rei Suo,
• Raku Irie,
• Hinako Nakayama,
• Yuta Ishimaru,
• Yuya Akama,
• Masato Oikawa and
• Shiro Itoi

Beilstein J. Org. Chem. 2025, 21, 2243–2249, doi:10.3762/bjoc.21.171

• all compounds. In this study, we developed a method to determine the absolute configuration of the terminal MPO moiety with high accuracy and sensitivity by a combination of chemical degradation, chemical synthesis, and chiral LC–MS analysis. The applicability of this method was demonstrated through

• absolute configuration of scarce natural products, including heptavalinamide A [11] and poecillastrin C [12][13] by a combination of chemical degradation, chemical synthesis, and liquid chromatography–mass spectrometry (LC–MS) analysis. The 3-methylpent-4-en-2-ol (MPO) moiety is commonly found at the

Synthesis of N-doped chiral macrocycles by regioselective palladium-catalyzed arylation

• Shuhai Qiu and
• Junzhi Liu

Beilstein J. Org. Chem. 2025, 21, 1917–1923, doi:10.3762/bjoc.21.149

• Shuhai Qiu Junzhi Liu Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China State Key Laboratory of Synthetic Chemistry, HKU-CAS Joint Laboratory on New Materials and Shanghai-Hong Kong Joint Laboratory on Chemical Synthesis, The University of Hong Kong, Pokfulam

Fe-catalyzed efficient synthesis of 2,4- and 4-substituted quinolines via C(sp²)–C(sp²) bond scission of styrenes

• Prafull A. Jagtap,
• Manish M. Petkar,
• Vaishnavi R. Sawant and
• Bhalchandra M. Bhanage

Beilstein J. Org. Chem. 2025, 21, 1799–1807, doi:10.3762/bjoc.21.142

• approach in chemical synthesis and drug discovery. Representative examples of bioactive quinolines. C(sp2)–C(sp2) bond-cleavage strategies for quinoline synthesis. Substrate scope of various arylamines and styrenes. Scale-up studies for the synthesis of antifungal agents. Mechanistic investigations

Approaches to stereoselective 1,1'-glycosylation

• Daniele Zucchetta and
• Alla Zamyatina

Beilstein J. Org. Chem. 2025, 21, 1700–1718, doi:10.3762/bjoc.21.133

• , the chemical synthesis of thiotrehalose analogs [116][117] provides a versatile tool for the construction of therapeutically relevant ligands or inhibitors of carbohydrate-specific innate immune receptors. Synthetic thiodigalactosides and their derivatives have been identified as selective inhibitors

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

• the foundational work of Kulkarni, Codée, Boons, and other outstanding groups in their studies on zwitterionic polysaccharides [7][8][9][10][11][12]. Pyruvylation of carbohydrate diols is commonly achieved through acetal substitution in the presence of acid during chemical synthesis. In this process

• for O4-linked synthesis in preparing various PS A1 derivatives. In our research, we carried out the synthesis of the PSA1 molecule as part of a broader effort to validate chemical synthesis methodologies. This work involved verifying our experimental techniques and understanding the underlying

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

• scaffold. The chemical synthesis, photophysical properties and suitability for barium tagging will be published in due course. Two possible double beta decay modes. Left: with emission of two electronic antineutrinos (ββ2ν). Right: neutrinoless double beta decay (ββ0ν). General structure of first

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

• Academy of Sciences, Kunming 650201, China 10.3762/bjoc.21.122 Abstract Chemical synthesis of monophosphorylated glycan motifs from the antitumor agent PI-88 has been achieved through an orthogonal one-pot glycosylation strategy on the basis of glycosyl ortho-(1-phenylvinyl)benzoates, which not only

• glycosylation, respectively; 2) synthesis of PI-88 glycan motif pentasaccharide via [1 + 1 + 1] and [1 + 1 + 3] one-pot orthogonal glycosylation; 3) synthesis of hexasaccharide via [1 + 1 + 1] and [1 + 1 + 1 + 3] one-pot assembly. Keywords: carbohydrates; chemical synthesis; glycosyl ortho-(1-phenylvinyl

• ]. Here, we report the chemical synthesis of monophosphorylated glycan motifs 1–4 from PI-88 through an orthogonal one-pot glycosylation strategy via strategic combinations of glycosyl N-phenyltrifluoroacetimidates (PTFAI) [57][58], glycosyl ortho-(alkynylbenzoates) [59][60] (ABz), and glycosyl PVB, which

Heterologous biosynthesis of cotylenol and concise synthesis of fusicoccane diterpenoids

• Ye Yuan,
• Zhenhua Guan,
• Xue-Jie Zhang,
• Nanyu Yao,
• Wenling Yuan,
• Yonghui Zhang,
• Ying Ye and
• Zheng Xiang

Beilstein J. Org. Chem. 2025, 21, 1489–1495, doi:10.3762/bjoc.21.111

• enzymatic terpene cyclization and chemical synthesis [30][31][32][33]. Briefly, the carbon scaffolds are forged by terpene cyclases, followed by concise chemical transformations to yield the desired natural products. Here, we describe heterologous biosynthesis of cotylenol by engineering the biosynthetic

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

• with pressurized gases (0.01–0.1 kbar). The first reports of using HHP were related to food industry applications [3][4], and later in chemical synthesis [5][6]. While the technique had been known since the late 1800s, and it had become popular in materials science and inorganic synthesis, it has

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

• chemistry [108][109]. Ultra-high vacuum (UHV) conditions on metallic surface allow to observe chemical species which are very reactive and impossible to isolate using classical chemical synthesis. Therefore, it is not surprising that such synthetic techniques have been applied to the synthesis of azulene

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

• reliable regioselectivity predictions that are essential for accelerating innovation in materials science and medicinal chemistry. Keywords: C–H activation; chemical synthesis planning; directing groups; quantum mechanics; regioselectivity prediction; Introduction The activation and functionalization of

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

• into fragment synthesis, providing a more holistic perspective on borrelidin’s chemical synthesis and biological relevance [50]. However, in-depth works focusing on key fragment optimizations remain limited. Hence, this review aims to address this gap. Review Syntheses of borrelidin fragments Uguen’s

Recent total synthesis of natural products leveraging a strategy of enamide cyclization

• Chun-Yu Mi,
• Jia-Yuan Zhai and
• Xiao-Ming Zhang

Beilstein J. Org. Chem. 2025, 21, 999–1009, doi:10.3762/bjoc.21.81

• , these reactions – particularly tandem processes – are highly effective in constructing both fused and bridged ring systems, offering valuable new tools for chemical synthesis. Future advancements in the field could involve further applications of enamide cyclizations with other nucleophiles or in

Recent advances in controllable/divergent synthesis

• Jilei Cao,
• Leiyang Bai and
• Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

• discipline and pursue novel advancements in the realm of chemical synthesis. Keywords: controllable; divergent; diverse products; switchable synthesis; Introduction In the era of synthetic organic chemistry, divergence can produce stereodivergence (including diastereodivergence and enantiodivergence) [1][2

• tactics in chemical synthesis. Ligand-controlled regiodivergent C1 insertion into arynes [19]. Ligand effect in homogenous gold catalysis enabling regiodivergent π-bond-activated cyclization [20]. Ligand-controlled palladium(II)-catalyzed regiodivergent carbonylation of alkynes [21]. Catalyst-controlled

Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning

• Pablo Quijano Velasco,
• Kedar Hippalgaonkar and
• Balamurugan Ramalingam

Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3

• demands solutions that meet multiple targets, such as yield, selectivity, purity, cost, environmental impact, etc. In recent years, the advancement of artificial intelligence (AI), machine learning (ML), and automation has produced a paradigm shift for chemical synthesis optimization techniques. By

• consonant and/or conflicting targets. In addition, the incorporation of lab robotics into chemical synthesis has enabled the development of closed-loop optimization platforms capable of executing optimization campaigns rapidly with minimal human intervention, relieving experimenters from labor-intensive

• trends in the selection of optimization algorithms for chemical synthesis. Finally, we highlight the future directions and opportunities in the field. For an in-depth overview on the topic of chemical reaction optimization, the readers are referred to prominent reviews by Taylor et al. [5], Griffin et al

Surprising acidity for the methylene of 1,3-indenocorannulenes?

• Shi Liu,
• Märt Lõkov,
• Sofja Tshepelevitsh,
• Ivo Leito,
• Kim K. Baldridge and
• Jay S. Siegel

Beilstein J. Org. Chem. 2024, 20, 3144–3150, doi:10.3762/bjoc.20.260

• an “azacorannulene”. Working from graph structures based on chemically stable (“group elementary”) nodes is a useful principle in molecular design and chemical synthesis. Such a perspective is important to understand fundamental physical organic molecular properties as well as to predict desirable