Themed collection Celebrating the 100th birthday of Professor Sukh Dev
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N-Heterocyclic carbene/palladium synergistic catalysis in organic synthesis
This review summarizes the progress made in the area of synergistic catalysis with N-heterocyclic carbenes and palladium.
Org. Biomol. Chem., 2024,22, 4613-4624
https://doi.org/10.1039/D4OB00525B
Natural products from the human microbiome: an emergent frontier in organic synthesis and drug discovery
The current landscape of synthetic campaigns and drug discovery initiatives focused on human microbiome-derived natural products is presented.
Org. Biomol. Chem., 2024,22, 4006-4030
https://doi.org/10.1039/D4OB00236A
Phenyliodine bis(trifluoroacetate) as a sustainable reagent: exploring its significance in organic synthesis
This research article highlights PIFA's versatility in organic synthesis, emphasizing its role in enabling diverse reactions and promoting its eco-friendly attributes over heavy transition metals.
Org. Biomol. Chem., 2024,22, 3109-3185
https://doi.org/10.1039/D3OB01964K
Recent advancement in the synthesis of quinoline derivatives via multicomponent reactions
This review highlights recent advancements in the synthesis of various quinoline derivatives through a multi-component approach involving different types of catalysts and catalyst-free reactions.
Org. Biomol. Chem., 2024,22, 2339-2358
https://doi.org/10.1039/D4OB00034J
Photocatalytic C2-trifluoroethylation and perfluoroalkylation of 3-substituted indoles using fluoroalkyl halides
A photocatalytic route towards 2-trifluoroethylated and 2-perfluoroalkylated indoles is reported. This transition-metal-free protocol employs simple fluoroalkyl halide precursors and works under mild conditions.
Org. Biomol. Chem., 2024,22, 4278-4282
https://doi.org/10.1039/D4OB00392F
Biomimetic total syntheses of renifolin F and antiarone K
The utilization of InCl3·4H2O as a mediator in the crucial step represents a novel procedure, particularly in prenylated systems, resulting primarily in the formation of a tertiary alcohol.
Org. Biomol. Chem., 2024, Advance Article
https://doi.org/10.1039/D4OB00651H
Photoinduced metal-free trifluoro/perfluoroalkylation of heteroarenes
A practical and straightforward protocol to access trifluoromethylated/perfluoroalkylated heteroarenes via radical-type nucleophilic substitution rather than typical radical-type electrophilic substitution is described here.
Org. Biomol. Chem., 2024,22, 4072-4076
https://doi.org/10.1039/D4OB00511B
Total synthesis of diplofuranone A and diapolic acid A
The first and concise syntheses of the anticancer agent diplofuranone A and the fatty acid-derived metabolite diapolic acid A have been demonstrated using easily accessible and commercially available starting materials.
Org. Biomol. Chem., 2024,22, 3589-3591
https://doi.org/10.1039/D4OB00433G
Cu(OTf)2/HFIP catalyzed regioselective cycloisomerization of indole-C3-functionalized alkynols to carbazoles
We report here a simple and atom economic cycloisomerization reaction of indole-tethered alkynols for constructing diverse carbazoles via 1,2-alkly migration using Cu(OTf)2/HFIP as the excellent promoter system.
Org. Biomol. Chem., 2024,22, 3622-3629
https://doi.org/10.1039/D4OB00421C
Bi(OTf)3-promoted cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters for the construction of polycyclic bridged pyrano-furopyranones
An efficient protocol for constructing polycyclic bridged chromano-furopyranones and pyrano-furopyranones (related to bioactive natural products) via bismuth(III)-catalyzed cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters is presented.
Org. Biomol. Chem., 2024,22, 496-500
https://doi.org/10.1039/D3OB01862H
Chemodivergent phosphonylation of diazocarboxylates: light-on vs. light-off reactions
The reaction between a-diazocarboxylates and trialkylphosphites under thermal and photochemical conditions results into N–P and C–P bond formation, respectively. The diazo substrates act as electrophiles in the former case and as carbene precursors in the later case.
Org. Biomol. Chem., 2024, Advance Article
https://doi.org/10.1039/D4OB00573B
Visible-light promoted oxidative annulation of 2-naphthols with phenylglyoxal monohydrates toward hydroxy-naphthofuranone and its derivatives
Base-promoted oxidative annulation of 2-naphthols and phenylglyoxal monohydrate via a metal-free, visible light-mediated reaction is reported for the synthesis of hydroxy-naphthofuranone, naphthofuranone, and naphthofuran with a broad substrate scope.
Org. Biomol. Chem., 2024, Advance Article
https://doi.org/10.1039/D4OB00693C
Gold(I)-catalysed cyclisation of (E)-ketene-N,O-acetals: a synthetic route toward spiro-oxazole-γ-lactones
Access to spiro-α-iodo-γ-lactones via multidirectional consecutive double 5-exo-dig cyclization.
Org. Biomol. Chem., 2024,22, 4672-4679
https://doi.org/10.1039/D4OB00551A
Trivalent dialkylaminopyridine-catalyzed site-selective mono-O-acylation of partially-protected pyranosides
This work demonstrates trivalent tris-(3-N-methyl-N-pyridyl propyl)amine catalyzing the site-selective mono-O-acylation of glycopyranosides.
Org. Biomol. Chem., 2024, Advance Article
https://doi.org/10.1039/D4OB00599F
Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one
Naturally occurring sesquiterpenes having humulane frameworks are structurally intriguing and possess significant biological profiles.
Org. Biomol. Chem., 2024,22, 4478-4487
https://doi.org/10.1039/D4OB00393D
Bisindole-based small molecules as transmembrane anion transporters and potential anticancer agents
A bisindole-based transmembrane anion antiporter, selectively toxic to the MCF-7 cancer cells, where chloride transport-induced homeostasis disruption triggered mitochondrial membrane depolarization, ROS generation, and lysosomal deacidification.
Org. Biomol. Chem., 2024, Advance Article
https://doi.org/10.1039/D4OB00554F
Synthesis, characterization and photophysical studies of dual-emissive base-modified fluorescent nucleosides
This research marks a significant step forward, offering rare dual-emissive nucleosides with excellent quantum yields and Stokes shift values, filling a critical gap in the field of nucleoside chemistry.
Org. Biomol. Chem., 2024, Advance Article
https://doi.org/10.1039/D4OB00749B
A divergent one-pot thiol-Michael strategy to create β-thiophene-fused porphyrins
A one-pot thiol-Michael strategy was developed for the construction of diverse β-thiophene-fused 5,10,15,20-tetraarylporphyrins. These new porphyrins displayed a modest red-shifted electronic absorption in contrast to meso-tetraarylporphyrins.
Org. Biomol. Chem., 2024,22, 4369-4377
https://doi.org/10.1039/D4OB00598H
PIDA-promoted metal-free [3 + 2] heteroannulation of β-ketothioamides with 4-hydroxy coumarins: chemo-/regioselective access to furo[3,2-c]chromen-4-ones at room temperature
A viable protocol to access furo[3,2-c]chromen-4-ones engaging 4-hydroxy coumarins and thioamides and mediated by phenyliodine(III) diacetate at room temperature in a highly efficient manner is developed.
Org. Biomol. Chem., 2024,22, 4326-4331
https://doi.org/10.1039/D4OB00438H
Synthetic access to diverse thiazetidines via a one-pot microwave assisted telescopic approach and their interaction with biomolecules
Computationally revealed mechanistic pathway of one-pot telescopically approached thiazetidine synthesis revealed the formation of a single product. The position of alkyl substitution plays significant role to enhance biomolecular interactions.
Org. Biomol. Chem., 2024,22, 3249-3261
https://doi.org/10.1039/D4OB00075G
Lewis acid-catalyzed one-pot thioalkenylation of donor–acceptor cyclopropanes using in situ generated dithiocarbamates and propiolates
One-pot, four component thioalkenylation of donor–acceptor (D–A) cyclopropanes using in situ generated dithiocarbamates and propiolates catalyzed by Yb(OTf)3 is presented.
Org. Biomol. Chem., 2024,22, 1834-1838
https://doi.org/10.1039/D4OB00053F
Diastereoselective synthesis of trans-2,3-dihydroindoles via formal [4 + 1] annulation reactions of a sulfonium ylide
We have established an in situ generated sulfonium-ylide mediated annulation to construct 2,3-disubstituted-2,3-dihydroindoles and extended to construct dihydrobenzofurans.
Org. Biomol. Chem., 2024,22, 621-632
https://doi.org/10.1039/D3OB01793A
Two-step, high-yielding total synthesis of antibiotic pyrones
A simple two-step dialkylation protocol was developed to synthesize antibiotics photopyrones, pseudopyronines, and violapyrones from triacetate lactone in excellent yields.
Org. Biomol. Chem., 2024,22, 554-560
https://doi.org/10.1039/D3OB01923C
FeCl3-catalyzed regioselective ring-opening of aryl oxirane with 4-hydroxycoumarin for the synthesis of furo[3,2-c]coumarins
The regioselective ring-opening of aryl oxiranes was investigated with various 4-hydroxycoumarins in dimethyl sulfoxide in the presence of 20 mol% FeCl3 as a catalyst at 110 °C.
Org. Biomol. Chem., 2024,22, 95-105
https://doi.org/10.1039/D3OB01721D
About this collection
This collection guest edited by Professor J.S. Yadav (Indrashil University), Professor Vinod K. Singh (IIT Kanpur), Professor S.S.V. Ramasastry (IISER Mohali) and Professor Harry Kochat (University of Tennessee Health Science Center) celebrates the 100th birthday of Professor Sukh Dev. Please enjoy these articles from members of the scientific community he helped inspire.