Themed collection Celebrating the 100th birthday of Professor Sukh Dev
Professor (Dr) Sukh Dev: an iconic scientist with an innate sixth sense who radicalized natural product synthesis & organic chemistry
Harry Kochat, J. S. Yadav, Vinod K. Singh and S. S. V. Ramasastry introduce the special Organic & Biomolecular Chemistry themed collection celebrating the 100th birthday of Professor Sukh Dev.
Org. Biomol. Chem., 2024,22, 5466-5469
https://doi.org/10.1039/D4OB90071E
Thapsigargin: a promising natural product with diverse medicinal potential – a review of synthetic approaches and total syntheses
Thapsigargin, a sesquiterpene lactone, has been known to the practitioners of traditional medicines as a cure for rheumatic pain and female infertility. This review discusses synthetic approaches and total syntheses of thapsigargin reported to date.
Org. Biomol. Chem., 2024,22, 8551-8569
https://doi.org/10.1039/D4OB01239A
gem-Difluoroallene (DFA): an emerging versatile synthetic precursor to enable diverse fluorinated molecules
This review article presents a comprehensive overview of the latest progress in utilizing gem-difluoroallenes for selective additions, defluorination, as well as cycloaddition and cyclization reactions.
Org. Biomol. Chem., 2024,22, 8078-8096
https://doi.org/10.1039/D4OB01253D
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
Diastereoselective cyclopropanation of α,β-unsaturated carbonyl compounds with vinyl sulfoxonium ylides
Vinyl cyclopropane scaffolds were synthesized via a proline-catalysed multicomponent reaction involving vinyl sulfoxonium ylides, aldehydes, and indane 1,3-dione.
Org. Biomol. Chem., 2024,22, 6294-6307
https://doi.org/10.1039/D4OB00677A
A HMPA–H2O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones
A HMPA–water mediated protocol to access substituted-indenones through an oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides has been developed under metal- and base-free conditions.
Org. Biomol. Chem., 2024,22, 5891-5896
https://doi.org/10.1039/D4OB00966E
Enal-azomethine ylides: application in the synthesis of functionalized pyrroles
Novel enal-azomethine ylides derived from diazoenals and N-alkyl imines gave N-alkyl-3-formyl pyrroles. The new methodology was used in the short synthesis of biologically relevant pyrrolo[3,2-c]quinoline and pyrrolo[2,1-a]isoquinoline scaffolds.
Org. Biomol. Chem., 2024,22, 5734-5738
https://doi.org/10.1039/D4OB00859F
Phosphine-promoted intramolecular Rauhut–Currier/Wittig reaction cascade to access (hetero)arene-fused diquinanes
Phosphine promotes a one-pot intramolecular Rauhut–Currier/Wittig reaction cascade to deliver arene- and heteroarene-fused diquinanes. The method is quite general and its utility has been demonstrated through various post-synthetic modifications.
Org. Biomol. Chem., 2024,22, 5718-5723
https://doi.org/10.1039/D4OB00984C
Deciphering substitution effects on reductive hydroalkoxylation of alkynyl aminols for stereoselective synthesis of morpholines and 1,4-oxazepanes: total synthesis of tridemorph and fenpropimorph
Depending on the alkynyl-substitution, N-alkynyl aminols gave divergent outcomes of morpholines and 1,2-oxazepanes via reductive etherification. Further, the method was used for the total synthesis of the fungicides tridemorph and fenpropimorph.
Org. Biomol. Chem., 2024,22, 5529-5533
https://doi.org/10.1039/D4OB00855C
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., 2024,22, 4877-4881
https://doi.org/10.1039/D4OB00651H
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
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
cisPro stabilization in prolyl carbamates influenced by tetrel bonding interactions
NMR spectral and theoretical analyses of homologous prolyl carbamates reveal subtle charge transfer tetrel bonding interactions (TBIs), selectively stabilizing their cisPro rotamers.
Org. Biomol. Chem., 2024, Advance Article
https://doi.org/10.1039/D4OB01539H
Benzylamine promoted direct C–H arylation of arenes and heteroarenes via excitation with heat or light
The combination of benzylamine, potassium tert-butoxide and 18-crown-6 acts as an excellent catalytic medium for the C–H arylation of arenes or heteroarenes with aryl or heteroaryl iodides/bromides under heating or light irradiation.
Org. Biomol. Chem., 2024, Advance Article
https://doi.org/10.1039/D4OB01377H
Rapid paper-based optical sensing of Spilosoma obliqua nucleopolyhedrovirus via ester hydrolysis
We have developed an easily scalable chromogenic probe for the dual-mode sensing of Spilosoma obliqua Nuclear polyhedrosis viruses (SpobNPV) in aqueous media.
Org. Biomol. Chem., 2024,22, 7841-7847
https://doi.org/10.1039/D4OB00582A
Shining light for organophotocatalysed site-selective sulfonylation of anilides
An organophotocatalytic approach for the site-selective sulfonylation of C(sp2)–H bonds of anilide and quinoline amide derivatives utilizing aryl sulfonyl chlorides as a sulfonylating agent is developed.
Org. Biomol. Chem., 2024,22, 7690-7695
https://doi.org/10.1039/D4OB01169D
Design of substituted tetrahydrofuran derivatives for HIV-1 protease inhibitors: synthesis, biological evaluation, and X-ray structural studies
A series of potent HIV-1 protease inhibitors with novel P2-ligands have been designed, synthesized and evaluated.
Org. Biomol. Chem., 2024,22, 7354-7372
https://doi.org/10.1039/D4OB00506F
A relay ring-closing metathesis/Diels–Alder approach to sugar-derived pluramycin-hybrids
Herein, we present a general approach involving a sequential relay ring-closing enyne metathesis, Diels–Alder, and oxidative aromatization reactions to synthesize pluramycinone-sugar hybrids.
Org. Biomol. Chem., 2024,22, 6727-6741
https://doi.org/10.1039/D4OB01049C
Expedient, regioselective C–H chalcogenation of 3,4-dihydro-1,4-benzoxazines using a palladium–copper catalyst
Palladium-catalyzed chalcogenation of benzoxazines has been achieved. The reaction shows broad substrate scope and late-stage functionalization potential. The regioselective product formation occurrs through a palladacycle.
Org. Biomol. Chem., 2024,22, 5809-5815
https://doi.org/10.1039/D4OB00524D
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., 2024,22, 5314-5324
https://doi.org/10.1039/D4OB00693C
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., 2024,22, 5224-5228
https://doi.org/10.1039/D4OB00573B
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., 2024,22, 5134-5149
https://doi.org/10.1039/D4OB00599F
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., 2024,22, 4987-4992
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., 2024,22, 4922-4939
https://doi.org/10.1039/D4OB00749B
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
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
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.