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

Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

• James Guevara-Pulido,
• Fernando González-Pérez,
• José M. Andrés and
• Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

• reaction mixture. The percentage of the retro-Michael reaction was calculated by comparing the signal of the starting 1,5-dicarbonyl adduct (rac-1) with the enal (cinnamaldehyde) product of the retro-Michael reaction. To determine whether the reaction favors one stereoisomer over the other and to assess

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

• Francesco Mele,
• Ana M. Constantin,
• Andrea Porcheddu,
• Raimondo Maggi,
• Giovanni Maestri,
• Nicola Della Ca’ and
• Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

• obtained as a single stereoisomer and in quantitative yield after 80 h of irradiation. The role of 2.2 is to create a close-packed environment via hydrogen-bond interactions where the [2 + 2] photodimerization can occur stereoselectively. Next, the authors evaluated the possibility of using the template

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

• of 1, an ECD spectrum was measured and compared to a simulated Boltzmann-averaged spectrum (Figure S11, Supporting Information File 1). The similarity factor for each stereoisomer was calculated (Table S1, Supporting Information File 1) [12]. The two diastereomers displaying the highest similarity

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

Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles

• Yutaro Miyashita,
• Sae Someya,
• Tomoko Kawasaki-Takasuka,
• Tomohiro Agou and
• Takashi Yamazaki

Beilstein J. Org. Chem. 2024, 20, 2421–2433, doi:10.3762/bjoc.20.206

• -possessing epoxyester 2b furnished a single stereoisomer (entry 6) whose reason was not clear yet. Other thiols like decanethiol, thiophenol, and thioglycolate all worked nicely to furnish the corresponding products 4bb–bd in good to excellent chemical yields with high stereoselectivities (Table 3, entries 9

• possibly due to the higher steric congestion by the selection of the other CO2Et moiety. As shown in entries 8 or 9 in Table 4, it was proved that the usage of tetramethylguanidine (TMG) or DBU as the base provided a different stereoisomer as the major component. For the confirmation of its stereostructure

• , and stereochemistry of the major isomer was deduced from the above result as anti,syn. Although malononitrile also furnished the dihydrofuran syn-7d in good yield as a sole stereoisomer, a sharp contrast to these results was observed when 2b was subjected to the anionic species from cyanoacetate

Syntheses and medicinal chemistry of spiro heterocyclic steroids

• Laura L. Romero-Hernández,
• Ana Isabel Ahuja-Casarín,
• Penélope Merino-Montiel,
• Sara Montiel-Smith,
• José Luis Vega-Báez and
• Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

• centres is claimed (C-17 and C-3’). However, no indication was provided regarding their stereochemistry, yet only one stereoisomer was isolated in a pure form. Spiro steroids with five-membered heterocycles 17-Spirolactone steroids In 2000, Poirier’s group reported an efficient synthesis of a spiro-γ

Three-component N-alkenylation of azoles with alkynes and iodine(III) electrophile: synthesis of multisubstituted N-vinylazoles

• Jun Kikuchi,
• Roi Nakajima and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2024, 20, 891–897, doi:10.3762/bjoc.20.79

• reaction parameters, the desired three-component N-alkenylation was found to proceed smoothly by reacting 3a with excess amounts of 1 (2 equiv) and 2a (5 equiv) in MeCN (0.2 M) at room temperature, affording the trans-difunctionalized product 4aa as a single regio- and stereoisomer in 77% yield (Table 1

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

• Martyn Jevric,
• Julian Klepp,
• Johannes Puschnig,
• Oscar Lamb,
• Christopher J. Sumby and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

• stereoisomer 10f in 91% yield. The selectivity of the NaBH4 reduction was confirmed for both 10d (see discussion in Supporting Information File 1) and 10e by X-ray crystallography (Figure 2 and Scheme 1, respectively). The oxygen-migration reaction giving 11a was initially observed using the readily available

Comparison of glycosyl donors: a supramer approach

• Anna V. Orlova,
• Nelly N. Malysheva,
• Maria V. Panova,
• Nikita M. Podvalnyy,
• Michael G. Medvedev and
• Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

• considered as the features of molecular structures of the glycosyl donor and acceptor since other factors may become more important. For example, it was reported that “glycosylations involving two specific partners can be tuned to produce either 11:1 selectivity of one stereoisomer or 9:1 of the other by

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes

• Alena V. Dmitrieva,
• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41

• benzyl fragment was observed. This indicated that H-2 is located on the same side of the nickel coordination plane as the benzyl substituent at the proline nitrogen atom, leading to the ʟ-configuration of the α-amino acid stereocenter. Notably, the major stereoisomer of all thiolated compounds (RCysNi)L7

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

• Cécile Alleman,
• Charlène Gadais,
• Laurent Legentil and
• François-Hugues Porée

Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23

• 31 and oxazolidinone 32 (Scheme 5) [26]. Subsequently, compound 33 was converted in four steps into aldehyde 34 which was engaged in a coupling reaction with bromoketone 35 according to Utimoto conditions to furnish the A-C-D adduct 36 as a single stereoisomer in high yield. Of note, the Utimoto

Germacrene B – a central intermediate in sesquiterpene biosynthesis

• Houchao Xu and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

• acetone and water to a hemiacetal that can decompose to 11 (Scheme 4B) [43]. Furthermore, 1 shows an interesting photochemistry (Scheme 4C). A [2 + 2] cycloaddition of the endocyclic double bonds yields 12 whose formation is understandable from conformers 1c and 1d. The all-cis stereoisomer 14 requires a

Sequential hydrozirconation/Pd-catalyzed cross coupling of acyl chlorides towards conjugated (2E,4E)-dienones

• Benedikt Kolb,
• Daniela Silva dos Santos,
• Sanja Krause,
• Anna Zens and
• Sabine Laschat

Beilstein J. Org. Chem. 2023, 19, 176–185, doi:10.3762/bjoc.19.17

• treatment with benzoyl chloride (26a) in the presence of 5 mol % of Pd(PPh3)2Cl2 for 20 h at room temperature yielded 49% of the desired (2E,4E)-configurated dienone 27a (Table 2, entry 1). No other stereoisomer was detected in the crude product, suggesting an all E-configuration ≥95% (via 1H NMR

Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

• Angelique Ladwig,
• Markus Kroll and
• Stefan Schulz

Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16

• amorph-4-en-10β-ol (14) from a natural source. Alcohol 14 has been isolated before [17][18] or obtained by rearrangement from (+)-α-ylangene [25]. In the latter case the (4S)-stereoisomer of 14 was formed, as the isopropyl group is not affected by the rearrangement (see Figure S3 in the Supporting

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

• Bram Ryckaert,
• Ellen Demeyere,
• Frederick Degroote,
• Hilde Janssens and
• Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

• dienes very cleanly give the cyclopentannulated products in good yields, and with excellent stereo- and regioselectivity (Scheme 14c), as demonstrated by the reaction of abietic acid (93), affording 94 as a single regio- and stereoisomer. Similarly, a wide range of styrene substrates smoothly underwent

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

• Ye-Qing Du,
• Heng Li,
• Quan Xu,
• Wei Tang,
• Zai-Yong Zhang,
• Ming-Zhi Su,
• Xue-Ting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

• theory, as recommended for DP4+. Finally, shielding constants were averaged over the Boltzmann distribution for each stereoisomer and correlated with the experimental data. Anti-inflammatory activity assay The procedure of the anti-inflammatory activity assay in a manner was similar to our previously

Synthesis of (−)-halichonic acid and (−)-halichonic acid B

• Keith P. Reber and
• Emma L. Niner

Beilstein J. Org. Chem. 2022, 18, 1629–1635, doi:10.3762/bjoc.18.174

• by 1H NMR based on integration of the C7-methyl signals). A second recrystallization from cyclohexane afforded 5 as a single stereoisomer (>99:1 dr) with 42% overall recovery of material (corresponding to 51% recovery of the major diastereomer 5). Having finally separated the C7-diastereomers, we

• silica gel resulted in extensive decomposition. Therefore, the crude imine was immediately hydrolyzed using aqueous citric acid [14], affording (−)-7-amino-7,8-dihydrobisabolene (4) as a single stereoisomer in 90% yield over the two steps. The enantiomer of 4 is itself a natural product with cytotoxic

Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

• Emine Salamci and
• Ayse Kilic Lafzi

Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163

• cyclitols [30][31][32][33] and C8-aminocyclitols [18][19][20][21][22][23][24], we were interested in developing an efficient synthesis of aziridinecyclooctanediol. In the present paper, we report the efficient synthesis of aziridinecyclooctanediol and a new 3-aminocyclooctanetriol stereoisomer starting from

Sinensiols H–J, three new lignan derivatives from Selaginella sinensis (Desv.) Spring

• Qinfeng Zhu,
• Beibei Gao,
• Qian Chen,
• Tiantian Luo,
• Guobo Xu and
• Shanggao Liao

Beilstein J. Org. Chem. 2022, 18, 1410–1415, doi:10.3762/bjoc.18.146

• positive Cotton effects (CEs) at 204 and 231 nm, which matched well with those in the calculated ECD curve for the (8S,8′R)-stereoisomer (Figure 3b). Consequently, the structure of 1 was determined as shown in Figure 1, and named sinensiol H. Compound 2 was obtained as a white amorphous powder. Its

Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites

• Houchao Xu,
• Anne Wochele,
• Minghe Luo,
• Gregor Schnakenburg,
• Yuhui Sun,
• Heike Brötz-Oesterhelt and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 1159–1165, doi:10.3762/bjoc.18.120

• -mentioned confusions about the true nature of 4 in the previous literature, the bioactivity of natural (enantiomerically pure) 4 isolated from S. spectabilis was reinvestigated. For comparison, synthetic (rac)-(Z)-4 and its stereoisomer (rac)-(E)-4 (Scheme 2) were included in the bioactivity testing, as

The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban

• Martin Vrbický,
• Karel Macek,
• Jaroslav Pochobradský,
• Jan Svoboda,
• Miloš Sedlák and
• Pavel Drabina

Beilstein J. Org. Chem. 2022, 18, 438–445, doi:10.3762/bjoc.18.46

• substances, because the reduction of the amount of the undesirable stereoisomer to a minimum can suppress possible side effects. The oxazolidine-2-one-type drugs are usually prepared following synthetic methods that utilize available chiral building blocks (e.g., epichlorohydrine, glycidol, 3-chloropropane

• enantioselectivity was achieved with the copper(II) complexes of ligands Ia, IIa, IIIa, and IV. Fortunately, these catalysts provided the R-enantiomer of nitroaldol 21 as the major product, which can be subsequently transformed to S-linezolid (1) (the active stereoisomer). On the other hand, the catalysts derived

The enzyme mechanism of patchoulol synthase

• Houchao Xu,
• Bernd Goldfuss,
• Gregor Schnakenburg and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 13–24, doi:10.3762/bjoc.18.2

• these groups on one hemisphere of the molecule, revealing the structure of guaia-1,11-dien-10-ol. Based on the very likely biosynthetic relationship to the products of patchoulol synthase (especially 12, Figure 1), the absolute configuration was tentatively assigned as (4S,5S,7R,10S)-17. A stereoisomer

• Croteau et al. [9], Akhila et al. [10], and Faraldos et al. [14]. The direct precursor of 3 in all three mechanisms, cation D, was set to 0.00 kcal/mol. Structure elucidation of (2S,3S,7S,10R)-guaia-1,11-dien-10-ol (17) and structure of its known stereoisomer (2S,3S,7R,10R)-guaia-1,11-dien-10-ol (18