Themed collection Celebrating the 100th birthday of Professor Sukh Dev

39 items
Editorial

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.

Graphical abstract: Professor (Dr) Sukh Dev: an iconic scientist with an innate sixth sense who radicalized natural product synthesis & organic chemistry
Review Article

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.

Graphical abstract: Thapsigargin: a promising natural product with diverse medicinal potential – a review of synthetic approaches and total syntheses
Review Article

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.

Graphical abstract: gem-Difluoroallene (DFA): an emerging versatile synthetic precursor to enable diverse fluorinated molecules
Open Access Review Article

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.

Graphical abstract: N-Heterocyclic carbene/palladium synergistic catalysis in organic synthesis
Review Article

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.

Graphical abstract: Natural products from the human microbiome: an emergent frontier in organic synthesis and drug discovery
Review Article

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.

Graphical abstract: Phenyliodine bis(trifluoroacetate) as a sustainable reagent: exploring its significance in organic synthesis
Review Article

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.

Graphical abstract: Recent advancement in the synthesis of quinoline derivatives via multicomponent reactions
Communication

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.

Graphical abstract: Diastereoselective cyclopropanation of α,β-unsaturated carbonyl compounds with vinyl sulfoxonium ylides
Communication

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.

Graphical abstract: A HMPA–H2O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones
Communication

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.

Graphical abstract: Enal-azomethine ylides: application in the synthesis of functionalized pyrroles
Communication

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.

Graphical abstract: Phosphine-promoted intramolecular Rauhut–Currier/Wittig reaction cascade to access (hetero)arene-fused diquinanes
Communication

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.

Graphical abstract: Deciphering substitution effects on reductive hydroalkoxylation of alkynyl aminols for stereoselective synthesis of morpholines and 1,4-oxazepanes: total synthesis of tridemorph and fenpropimorph
Communication

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.

Graphical abstract: Biomimetic total syntheses of renifolin F and antiarone K
Communication

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.

Graphical abstract: Photocatalytic C2-trifluoroethylation and perfluoroalkylation of 3-substituted indoles using fluoroalkyl halides
Communication

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.

Graphical abstract: Photoinduced metal-free trifluoro/perfluoroalkylation of heteroarenes
Communication

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.

Graphical abstract: Total synthesis of diplofuranone A and diapolic acid A
Communication

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.

Graphical abstract: Cu(OTf)2/HFIP catalyzed regioselective cycloisomerization of indole-C3-functionalized alkynols to carbazoles
Communication

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.

Graphical abstract: Bi(OTf)3-promoted cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters for the construction of polycyclic bridged pyrano-furopyranones
Paper

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.

Graphical abstract: cisPro stabilization in prolyl carbamates influenced by tetrel bonding interactions
Paper

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.

Graphical abstract: Benzylamine promoted direct C–H arylation of arenes and heteroarenes via excitation with heat or light
Paper

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.

Graphical abstract: Rapid paper-based optical sensing of Spilosoma obliqua nucleopolyhedrovirus via ester hydrolysis
Paper

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.

Graphical abstract: Shining light for organophotocatalysed site-selective sulfonylation of anilides
Paper

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.

Graphical abstract: Design of substituted tetrahydrofuran derivatives for HIV-1 protease inhibitors: synthesis, biological evaluation, and X-ray structural studies
Paper

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.

Graphical abstract: A relay ring-closing metathesis/Diels–Alder approach to sugar-derived pluramycin-hybrids
Paper

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.

Graphical abstract: Expedient, regioselective C–H chalcogenation of 3,4-dihydro-1,4-benzoxazines using a palladium–copper catalyst
Paper

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.

Graphical abstract: Visible-light promoted oxidative annulation of 2-naphthols with phenylglyoxal monohydrates toward hydroxy-naphthofuranone and its derivatives
Paper

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.

Graphical abstract: Chemodivergent phosphonylation of diazocarboxylates: light-on vs. light-off reactions
Paper

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.

Graphical abstract: Trivalent dialkylaminopyridine-catalyzed site-selective mono-O-acylation of partially-protected pyranosides
Paper

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.

Graphical abstract: Bisindole-based small molecules as transmembrane anion transporters and potential anticancer agents
Paper

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.

Graphical abstract: Synthesis, characterization and photophysical studies of dual-emissive base-modified fluorescent nucleosides
Paper

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.

Graphical abstract: Gold(i)-catalysed cyclisation of (E)-ketene-N,O-acetals: a synthetic route toward spiro-oxazole-γ-lactones
Paper

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.

Graphical abstract: Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one
Paper

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.

Graphical abstract: A divergent one-pot thiol-Michael strategy to create β-thiophene-fused porphyrins
Paper

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.

Graphical abstract: 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
Paper

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.

Graphical abstract: Synthetic access to diverse thiazetidines via a one-pot microwave assisted telescopic approach and their interaction with biomolecules
Paper

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.

Graphical abstract: Lewis acid-catalyzed one-pot thioalkenylation of donor–acceptor cyclopropanes using in situ generated dithiocarbamates and propiolates
Paper

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.

Graphical abstract: Diastereoselective synthesis of trans-2,3-dihydroindoles via formal [4 + 1] annulation reactions of a sulfonium ylide
Paper

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.

Graphical abstract: Two-step, high-yielding total synthesis of antibiotic pyrones
Paper

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.

Graphical abstract: FeCl3-catalyzed regioselective ring-opening of aryl oxirane with 4-hydroxycoumarin for the synthesis of furo[3,2-c]coumarins
39 items

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.

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