Diastereomer
View article: Synthesis and Characterization of Key Stereoisomers Related to Eluxadoline
Synthesis and Characterization of Key Stereoisomers Related to Eluxadoline Open
Eluxadoline is a novel active pharmaceutical ingredient (API) employed in the treatment of diarrhea and abdominal discomfort associated with diarrhea-predominant irritable bowel syndrome (IBS-D). Throughout the laboratory optimization and …
View article: Jahn-Teller Driven Stereoselectivity in Olefin Metathesis: Insights from Electronic Structure
Jahn-Teller Driven Stereoselectivity in Olefin Metathesis: Insights from Electronic Structure Open
Olefin metathesis has revolutionized synthetic chemistry by providing powerful tools for carbon-carbon double bond formation, yet controlling the stereoselectivity of the newly formed olefins remains a significant challenge. While thermody…
View article: Jahn-Teller Driven Stereoselectivity in Olefin Metathesis: Insights from Electronic Structure
Jahn-Teller Driven Stereoselectivity in Olefin Metathesis: Insights from Electronic Structure Open
Olefin metathesis has revolutionized synthetic chemistry by providing powerful tools for carbon-carbon double bond formation, yet controlling the stereoselectivity of the newly formed olefins remains a significant challenge. While thermody…
View article: Structural Interconversions and Guest Binding Properties of Tetrakis(formylpyridine)-Based <i>Pseudo</i> -Cubic and Trigonal-Prismatic Metal–Organic Capsules
Structural Interconversions and Guest Binding Properties of Tetrakis(formylpyridine)-Based <i>Pseudo</i> -Cubic and Trigonal-Prismatic Metal–Organic Capsules Open
Here, we report a new tetrakis(formylpyridine) subcomponent that was designed to assemble with anilines and ZnII to afford a set of structurally distinct metal-organic cage structure types. By modulating the metal-to-ligand stoi…
View article: Oxidative degradation of alpha-tocopherol by reactive oxygen species, identifying products, and product anticancer activity
Oxidative degradation of alpha-tocopherol by reactive oxygen species, identifying products, and product anticancer activity Open
View article: Chemistry of Herbarumin I, Stagonolide A and Structurally Related Phytotoxic Ten-Membered Lactones: Oxidative Cleavage, Stereospecific Epoxidation, Transannulation and Dimerization (Preprint + supplementary and raw data)
Chemistry of Herbarumin I, Stagonolide A and Structurally Related Phytotoxic Ten-Membered Lactones: Oxidative Cleavage, Stereospecific Epoxidation, Transannulation and Dimerization (Preprint + supplementary and raw data) Open
Ten-membered lactones (TMLs) produced by phytopathogenic fungi are considered as model compounds for the development of nature-inspired agrochemicals with novel mechanisms of action. Despite their structural simplicity, TMLs display a broa…
View article: Stereoisomeric Separation of Flavonoids by Two‐Dimensional Supercritical Fluid Chromatography: Identification of Adequate Chiral Columns and Application to Honey Analysis
Stereoisomeric Separation of Flavonoids by Two‐Dimensional Supercritical Fluid Chromatography: Identification of Adequate Chiral Columns and Application to Honey Analysis Open
Chiral flavonoids are frequently encountered in natural products consumed as food or therapeutic products. However, the taste and other bioactivities of stereoisomers are known to differ. Hence, stereoseparation methods are necessary to re…
View article: Dendritic Pillar[6]Arenes with Fixed Planar Chirality for Stereoselective Inclusions in Water: A Case of Facile Differentiation of Cocaine Adulterants, Levamisole and Dexamisole
Dendritic Pillar[6]Arenes with Fixed Planar Chirality for Stereoselective Inclusions in Water: A Case of Facile Differentiation of Cocaine Adulterants, Levamisole and Dexamisole Open
We describe the preparation, conformational dynamics, and stereoselective recognition characteristics of water‐soluble pillar[6]arenes pS – 2 12− and pR – 2 12− . These two novel and diastereomeric cavitands comprise a 2,5‐ bis (ethoxy)pil…
View article: To PLP or Not to PLP: Stereodivergent Transaminase-Catalyzed Reactions Directed by Kinetic and Thermodynamic Control
To PLP or Not to PLP: Stereodivergent Transaminase-Catalyzed Reactions Directed by Kinetic and Thermodynamic Control Open
Selective catalysis is a key objective in organic synthesis, and reactions with differing kinetic and thermodynamic products present the opportunity for divergent reaction outcomes with a single catalyst. We report a biocatalytic method in…
View article: A Straightforward Access to Enantiopure 4‐Hydroxy‐pipecolic Acid Peptidomimetics by aza‐Prins Cyclization/LiNTf <sub>2</sub> ‐Promoted Aminolysis of Lactones
A Straightforward Access to Enantiopure 4‐Hydroxy‐pipecolic Acid Peptidomimetics by aza‐Prins Cyclization/LiNTf <sub>2</sub> ‐Promoted Aminolysis of Lactones Open
Peptidomimetics, that can take advantage of bioavailability and metabolic stability, are considered as an important class of molecules and constitute thus a large research field in medicinal chemistry. With the aim of obtaining constrained…
View article: Lipase-Catalyzed Kinetic Resolution Followed by an Intramolecular Diels–Alder Reaction: Enantio- and Diastereoselective Synthesis of an A-Ring Moiety of Furanosteroids
Lipase-Catalyzed Kinetic Resolution Followed by an Intramolecular Diels–Alder Reaction: Enantio- and Diastereoselective Synthesis of an A-Ring Moiety of Furanosteroids Open
Furanosteroids are known to exhibit inhibitory activity against phosphatidylinositol-3-kinase and are expected to serve as a basis for the development of therapeutic drugs for various diseases. In this study, a novel protocol is presented …
View article: Anisotropic Nuclear Magnetic Resonance Spectroscopy and Density Functional Theory Methodologies Combine with CASE‐3D Analysis for Unambiguous Diastereomeric Differentiation of AMG 176 Macrocycles
Anisotropic Nuclear Magnetic Resonance Spectroscopy and Density Functional Theory Methodologies Combine with CASE‐3D Analysis for Unambiguous Diastereomeric Differentiation of AMG 176 Macrocycles Open
As the molecular complexity of active pharmaceutical ingredients (APIs) continues to rise, it is necessary for analytical chemists to evolve and develop robust analytical techniques to provide unambiguous structure identification and ensur…
View article: Rational Design, Synthesis and In Vitro Activity of Diastereomeric Cis-/Trans-3-Substituted-3,4-Dihydroisocoumarin-4-Carboxylic Acids as Potential Carnitine Acetyltransferase Inhibitors
Rational Design, Synthesis and In Vitro Activity of Diastereomeric Cis-/Trans-3-Substituted-3,4-Dihydroisocoumarin-4-Carboxylic Acids as Potential Carnitine Acetyltransferase Inhibitors Open
This study explores a series of 3,4-dihydroisocoumarins as potential inhibitors of fatty acid oxidation through rational design, synthesis and in vitro evaluation. The compounds studied were designed as structural analogs of the natural su…
View article: Diastereoselective synthesis of multi-substituted cyclobutanes via catalyst-controlled regiodivergent hydrophosphination of acyl bicyclobutanes
Diastereoselective synthesis of multi-substituted cyclobutanes via catalyst-controlled regiodivergent hydrophosphination of acyl bicyclobutanes Open
View article: A Supramolecular Extension of Mosher’s Method: Absolute Configuration Assignment of N-Amino Acid Derivatives via Bis-Thiourea Chiral Solvating Agent
A Supramolecular Extension of Mosher’s Method: Absolute Configuration Assignment of N-Amino Acid Derivatives via Bis-Thiourea Chiral Solvating Agent Open
The bis-thiourea chiral solvating agent (CSA) BTDA enables the NMR-based determination of absolute configuration in N-3,5-dinitrobenzoyl (DNB) amino acid derivatives without requiring covalent derivatization. A reliable trend of the sense …
View article: Rational Design, Synthesis and <em>In Vitro</em> Activity of Diastereomeric <em>Cis</em>-/<em>trans</em>-3-substituted-3,4- dihydroisocoumarin-4-carboxylic Acids as Potential Carnitine Acetyltransferase Inhibitors
Rational Design, Synthesis and <em>In Vitro</em> Activity of Diastereomeric <em>Cis</em>-/<em>trans</em>-3-substituted-3,4- dihydroisocoumarin-4-carboxylic Acids as Potential Carnitine Acetyltransferase Inhibitors Open
This study explores a series of 3,4-dihydroisocoumarins as potential inhibitors of fatty acid oxidation through rational design, molecular docking, synthesis, and in vitro evaluation. The compounds studied were designed as structural analo…
View article: A Facile Synthesis, Spectroscopic Identification, and Antimicrobial Activities of Some New Heterocyclic Derivatives from D-erythro-2,3-hexodiuloso-1,4-lactone-2-(o-chlorophenyl hydrazone)-3-oxime
A Facile Synthesis, Spectroscopic Identification, and Antimicrobial Activities of Some New Heterocyclic Derivatives from D-erythro-2,3-hexodiuloso-1,4-lactone-2-(o-chlorophenyl hydrazone)-3-oxime Open
A new series of different heterocyclic derivatives was prepared via a facile unimolecular condensation of D-iso ascorbic acid with o-chlorophenyl hydrazine to give D-erythro-2,3-hexodiulosono-1,4-lactone 2-( o-chlorophenyl hydrazine (2). R…
View article: Homologous Ladder Cyclohexasilanes
Homologous Ladder Cyclohexasilanes Open
We report the synthesis of five new examples of ladder cyclohexasilanes, possessing up to three consecutive fused rings and differing in relative ring fusion configuration and side chain structure. By coupling a 1,4‐dipotassiooligosilyl di…
View article: A Comparative DFT Study of the Chemical Reactivity of Diastereoisomers Cis/trans Clovamides and Derivatives, Isolated from <i>icacina</i><i> </i><i>mannii</i>
A Comparative DFT Study of the Chemical Reactivity of Diastereoisomers Cis/trans Clovamides and Derivatives, Isolated from <i>icacina</i><i> </i><i>mannii</i> Open
View article: Expedient Access to Cyclobutanones and Spirohexanones via Formal [3+1] Cycloaddition of Cyclopropanones with Sulfur Ylides
Expedient Access to Cyclobutanones and Spirohexanones via Formal [3+1] Cycloaddition of Cyclopropanones with Sulfur Ylides Open
A concise synthetic route to enantioenriched cyclobutanones is reported via ring expansion of cyclopropanone surrogates with unstabilized sulfoxonium ylides. The reaction is shown to proceed with complete regio- and stereospecificity with …
View article: Delta/Lambda Chirality: From Enantiomers to Diastereomers in Heterometallic Complexes with Chelating Ligands
Delta/Lambda Chirality: From Enantiomers to Diastereomers in Heterometallic Complexes with Chelating Ligands Open
The Δ/Λ chirality observed in octahedral molecules with chelating ligands represents the major group of "chiral-at-metal" complexes. Upon shifting from mononuclear to polynuclear systems with multiple (≥2) chiral centers, not only enantiom…
View article: Overcoming the challenge of confident identification among two related groups of 17-methyl steroids by GC-MS
Overcoming the challenge of confident identification among two related groups of 17-methyl steroids by GC-MS Open
Tetrahydromethyltestosterone (THMT) and 20 hydroxymethyl 18-nortetrahydromethyltestosterone (20OHnorTHMT) are metabolites of the anabolic androgenic steroids methyltestosterone and metandienone. Both molecule structures are used as markers…
View article: Rotational, vibrational, conformational and diastereomeric dimer cooling of aminoalcohols in soft supersonic expansions and the monohydrate of dimethylaminoethanol
Rotational, vibrational, conformational and diastereomeric dimer cooling of aminoalcohols in soft supersonic expansions and the monohydrate of dimethylaminoethanol Open
Supersonic jet expansions allow to cool molecules and to form molecular complexes over a wide range of expansion conditions, ranging from nearly effusive expansions of the pure vapour to colder expansions in carrier gases. The resulting mo…
View article: Crystal structure, computational study, and Hirshfeld analysis of <i>exo</i>-1,2,3,5-tetraphenyl-1a',9b'-dihydrospiro[bicyclo[3.1.0]hexane-6,1′-cyclopropa[<i>l</i>]phenanthren]-2-en-4-one
Crystal structure, computational study, and Hirshfeld analysis of <i>exo</i>-1,2,3,5-tetraphenyl-1a',9b'-dihydrospiro[bicyclo[3.1.0]hexane-6,1′-cyclopropa[<i>l</i>]phenanthren]-2-en-4-one Open
The reaction of dibenzonorcarynyliden(e/oid) with phencyclone was recently reported to give a congested spiropentane with endo stereochemistry. Herein we report that, in sharp contrast, an analogous reaction using tetracyclone, instead of …
View article: Isolation and Identification of Cis-2,5-Diketopiperazine from a Novel Bacillus Strain and Synthesis of Its Four Stereoisomers
Isolation and Identification of Cis-2,5-Diketopiperazine from a Novel Bacillus Strain and Synthesis of Its Four Stereoisomers Open
The Bacillus horneckiae-like strain 2011SOCCUF3 was isolated from the marine sponge Spongia officinalis and its metabolome was studied for secondary metabolites with antimicrobial activity. Culturing in the presence of Diaion HP-20 resin a…
View article: Mobility and Stability Enhancements of Conjugated Polymers with Diastereomeric Conjugation Break Spacers in Organic Electrochemical Transistors
Mobility and Stability Enhancements of Conjugated Polymers with Diastereomeric Conjugation Break Spacers in Organic Electrochemical Transistors Open
View article: Diastereoselective Transfer Hydrogenation of Cyclic and Bicyclic Ketones over Selected Metal Oxides as Catalysts
Diastereoselective Transfer Hydrogenation of Cyclic and Bicyclic Ketones over Selected Metal Oxides as Catalysts Open
The diastereoselectivity of the liquid- and vapor-phase Catalytic Transfer Hydrogenation (CTH) of cyclic ketones: x-methylcyclohexanones (x = 2, 3 or 4), 4-t-butylcyclohexanone, and bicyclic ketones: 2-norbornanone, camphor, fenchone, and …
View article: Organophotoredox-Catalyzed Stereoselective Synthesis of Bicyclo[3.2.0]heptanes via [2+2] Photocycloaddition
Organophotoredox-Catalyzed Stereoselective Synthesis of Bicyclo[3.2.0]heptanes via [2+2] Photocycloaddition Open
The stereoselective synthesis of bicyclo[3.2.0]heptanes via an anion radical [2+2] photocycloaddition of aryl bis-enone derivatives was investigated. By employing chiral oxazolidinone auxiliaries bound to aryl bis-enone substrates, enantio…
View article: Computational Exploration of Stereoelectronic Relationships in Manganese‐Catalyzed Hydrogenation Reactions
Computational Exploration of Stereoelectronic Relationships in Manganese‐Catalyzed Hydrogenation Reactions Open
Stereoelectronic effects governing Mn‐catalyzed hydrogenation reactions have been deconvoluted through the analysis of a series of in silico catalyst modifications using DFT (PBE0‐D3 PCM(EtOH) /def2‐TZVP//RI‐BP86 PCM(EtOH) /def2‐SVP level …
View article: Structure Confirmation of Quinazolinone and Hydroindole Using Residual Dipolar Couplings From Polyarylisocyanide Liquid Crystal
Structure Confirmation of Quinazolinone and Hydroindole Using Residual Dipolar Couplings From Polyarylisocyanide Liquid Crystal Open
Determining the constitution and configuration is a critical step in characterizing the structure of small molecules. In addition to the classical nuclear magnetic resonance (NMR) method conducted in isotropic solutions, the emerging aniso…