Varinder K. Aggarwal
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View article: Caylobolide B: Structure Revision, Total Synthesis, Biological Characterization, and Discovery of New Analogues
Caylobolide B: Structure Revision, Total Synthesis, Biological Characterization, and Discovery of New Analogues Open
The unique potential of marine polyhydroxylated macrolides in chemical biology and drug discovery has long been constrained by their structural complexity and limited material availability, frustrating efforts in stereochemical assignment,…
View article: Alkenyl- and Aryl-Borane Nucleophiles in Enantioselective Iridium-Catalyzed Allylic Substitution of Vinyl Epoxides
Alkenyl- and Aryl-Borane Nucleophiles in Enantioselective Iridium-Catalyzed Allylic Substitution of Vinyl Epoxides Open
The catalytic asymmetric Petasis reaction represents a practical approach for synthesizing highly valuable chiral amine building blocks. However, despite the potential that this reactivity provides, the extension of the mechanistic framewo…
View article: Synthesis of Indoloazepinone Scaffolds Using Sequential Photochemical and Photocatalytic Reactions
Synthesis of Indoloazepinone Scaffolds Using Sequential Photochemical and Photocatalytic Reactions Open
Indoloazepinone scaffolds show promise as anticancer compounds; however, current methods for their synthesis rely on azepinone ring formation from prefunctionalized indoles. Herein, we report an alternative strategy for the rapid synthesis…
View article: Intramolecular Lithiation‐Borylation for the Stereoselective Synthesis of Cyclopentyl and Cyclobutyl Bis‐Boronic Esters
Intramolecular Lithiation‐Borylation for the Stereoselective Synthesis of Cyclopentyl and Cyclobutyl Bis‐Boronic Esters Open
Saturated carbocycles are common motifs in natural products and pharmaceuticals, and so methods for their construction, particularly with high diastereo‐ and enantiocontrol, are of high importance. Lithiation‐borylation has emerged as powe…
View article: Intramolecular Lithiation‐Borylation for the Stereoselective Synthesis of Cyclopentyl and Cyclobutyl Bis‐Boronic Esters
Intramolecular Lithiation‐Borylation for the Stereoselective Synthesis of Cyclopentyl and Cyclobutyl Bis‐Boronic Esters Open
Saturated carbocycles are common motifs in natural products and pharmaceuticals, and so methods for their construction, particularly with high diastereo‐ and enantiocontrol, are of high importance. Lithiation‐borylation has emerged as powe…
View article: Boron-mediated modular assembly of tetrasubstituted alkenes
Boron-mediated modular assembly of tetrasubstituted alkenes Open
View article: Total Synthesis and Structure Determination of Mycapolyol E Using Iterative Homologation of Boronic Esters
Total Synthesis and Structure Determination of Mycapolyol E Using Iterative Homologation of Boronic Esters Open
Mycapolyol E is a cytotoxic polyketide synthase/nonribosomal peptide synthetase (PKS/NRPS) metabolite isolated from a marine sponge containing an extended polyacetate motif, terminal formamide moiety, and tetramic acid‐derived headgroup, w…
View article: Persistent Boryl Radicals as Highly Reducing Photoredox Catalysts for Debrominative Borylations
Persistent Boryl Radicals as Highly Reducing Photoredox Catalysts for Debrominative Borylations Open
Organic free radicals are commonly perceived to be highly reactive species with short lifetimes, yet there are many examples that defy this convention by displaying remarkable stability. Although these persistent radicals can be relatively…
View article: Breaking the “rule-of-five” to access Bridged Bicyclic Heteroaromatic Bioisosteres
Breaking the “rule-of-five” to access Bridged Bicyclic Heteroaromatic Bioisosteres Open
Bioisosteric replacement of aromatic and heteroaromatic rings with bridged bicyclic hydrocarbons is an important strategy in drug discovery. Intramolecular [2+2] cycloadditions of unconjugated dienes provide an efficient route to these mot…
View article: The combination of synthesis and ultra-high-resolution NMR spectroscopy reveals the correct structure of caylobolide A
The combination of synthesis and ultra-high-resolution NMR spectroscopy reveals the correct structure of caylobolide A Open
View article: A Simple NMR‐Based Rule for Stereochemical Assignment of 1,5‐Diols in Polyketides
A Simple NMR‐Based Rule for Stereochemical Assignment of 1,5‐Diols in Polyketides Open
Polyketide natural products are a valuable source of inspiration for therapeutic lead compounds, but their diversity and complexity make structure elucidation highly challenging. Here, we report a comprehensive analysis of the relative ste…
View article: Iridium-Catalyzed Stereocontrolled C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Cross-Coupling of Boronic Esters and Allylic Carbonates Enabled by Boron-to-Zinc Transmetalation
Iridium-Catalyzed Stereocontrolled C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Cross-Coupling of Boronic Esters and Allylic Carbonates Enabled by Boron-to-Zinc Transmetalation Open
The stereocontrolled C(sp3)-C(sp3) cross-coupling represents a considerable challenge of great contemporary interest. While this has been achieved through the reactions of boronate complexes with π-allyl iridium compl…
View article: Computation, Synthesis and NMR Investigations of PROTAC Linker Conformation, Chamaleonicity and their Impacts on the Mode of Action
Computation, Synthesis and NMR Investigations of PROTAC Linker Conformation, Chamaleonicity and their Impacts on the Mode of Action Open
Linker design is a core task in Proteolysis Targeting Chimera (PROTAC) drug discovery, which influences ternary complex formation for selective target protein degradation as well as physicochemical properties. However, it remains challengi…
View article: Merging Organocatalysis with 1,2-Boronate Rearrangement: A Lewis Base-Catalyzed Asymmetric Multicomponent Reaction
Merging Organocatalysis with 1,2-Boronate Rearrangement: A Lewis Base-Catalyzed Asymmetric Multicomponent Reaction Open
Catalytic asymmetric multicomponent 1,2-boronate rearrangements provide a practical approach for synthesizing highly valuable enantioenriched boronic esters. When applied to alkenyl or heteroaryl boronates, these reactions have relied main…
View article: Platinum‐Catalyzed Regio‐ and Enantioselective Diboration of Unactivated Alkenes with (pin)B−B(dan)
Platinum‐Catalyzed Regio‐ and Enantioselective Diboration of Unactivated Alkenes with (pin)B−B(dan) Open
Asymmetric diboration of terminal alkenes is well established, and subsequent selective functionalization of the less hindered primary boronic ester is commonly achieved. Conversely, selective functionalization of the sterically less acces…
View article: Synthesis of 1‐Azabicyclo[2.1.1]hexanes via Formal Single Electron Reduction of Azabicyclo[1.1.0]butanes under Photochemical Conditions
Synthesis of 1‐Azabicyclo[2.1.1]hexanes via Formal Single Electron Reduction of Azabicyclo[1.1.0]butanes under Photochemical Conditions Open
C(sp 3 )‐rich heterocycles are privileged building blocks for pharmaceuticals and agrochemicals. Therefore, synthetic methods that provide access to novel saturated nitrogen‐containing heterocycles are in high demand. Herein, we report a g…
View article: Synthesis of 1‐Azabicyclo[2.1.1]hexanes via Formal Single Electron Reduction of Azabicyclo[1.1.0]butanes under Photochemical Conditions
Synthesis of 1‐Azabicyclo[2.1.1]hexanes via Formal Single Electron Reduction of Azabicyclo[1.1.0]butanes under Photochemical Conditions Open
C(sp 3 )‐rich heterocycles are privileged building blocks for pharmaceuticals and agrochemicals. Therefore, synthetic methods that provide access to novel saturated nitrogen‐containing heterocycles are in high demand. Herein, we report a g…
View article: Difluorinated thromboxane A<sub>2</sub> reveals crosstalk between platelet activatory and inhibitory pathways by targeting both the TP and IP receptors
Difluorinated thromboxane A<sub>2</sub> reveals crosstalk between platelet activatory and inhibitory pathways by targeting both the TP and IP receptors Open
Background and Purpose Thromboxane A 2 (TXA 2 ) is a prostanoid produced during platelet activaton, important in enhancing platelet reactivity by activation of TP receptors. However, due to the short half‐life, studying TXA 2 signalling is…
View article: Simultaneous Stereoinvertive and Stereoselective C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Cross-Coupling of Boronic Esters and Allylic Carbonates
Simultaneous Stereoinvertive and Stereoselective C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Cross-Coupling of Boronic Esters and Allylic Carbonates Open
With increasing interest in constructing more three-dimensional entities, there has been growing interest in cross-coupling reactions that forge C(sp3)-C(sp3) bonds, which leads to additional challenges as it is not j…
View article: Cluster Preface: Modern Boron Chemistry: 60 Years of the Matteson Reaction
Cluster Preface: Modern Boron Chemistry: 60 Years of the Matteson Reaction Open
James P. Morken (left) was born in Concord, California (USA) and obtained his B.S. in chemistry in 1989 from UC Santa Barbara (USA) working with Prof. Bruce Rickborn. He obtained his Ph.D. from Boston College (USA) in 1995 with Prof. Amir…
View article: Stereospecific Conversion of Boronic Esters into Enones using Methoxyallene: Application in the Total Synthesis of 10‐Deoxymethynolide
Stereospecific Conversion of Boronic Esters into Enones using Methoxyallene: Application in the Total Synthesis of 10‐Deoxymethynolide Open
Enones are widely utilized linchpin functional groups in chemical synthesis and molecular biology. We herein report the direct conversion of boronic esters into enones using commercially available methoxyallene as a three‐carbon building b…
View article: Stereospecific Conversion of Boronic Esters into Enones using Methoxyallene: Application in the Total Synthesis of 10‐Deoxymethynolide
Stereospecific Conversion of Boronic Esters into Enones using Methoxyallene: Application in the Total Synthesis of 10‐Deoxymethynolide Open
Enones are widely utilized linchpin functional groups in chemical synthesis and molecular biology. We herein report the direct conversion of boronic esters into enones using commercially available methoxyallene as a three‐carbon building b…
View article: PB0410 Difluorinated Thromboxane A2 Reveals Crosstalk between Platelet Activatory and Inhibitory Pathways by Targeting Both the TP and IP Receptor
PB0410 Difluorinated Thromboxane A2 Reveals Crosstalk between Platelet Activatory and Inhibitory Pathways by Targeting Both the TP and IP Receptor Open
View article: CCDC 2216343: Experimental Crystal Structure Determination
CCDC 2216343: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Convergent Deboronative and Decarboxylative Phosphonylation Enabled by the Phosphite Radical Trap “BecaP”
Convergent Deboronative and Decarboxylative Phosphonylation Enabled by the Phosphite Radical Trap “BecaP” Open
Carbon-phosphorus bond formation is significant in synthetic chemistry because phosphorus-containing compounds offer numerous indispensable biochemical roles. While there is a plethora of methods to access organophosphorus compounds, phosp…
View article: Photoredox‐Catalyzed Decarboxylative Bromination, Chlorination and Thiocyanation Using Inorganic Salts
Photoredox‐Catalyzed Decarboxylative Bromination, Chlorination and Thiocyanation Using Inorganic Salts Open
Decarboxylative halogenation reactions of alkyl carboxylic acids are highly valuable reactions for the synthesis of structurally diverse alkyl halides. However, many reported protocols rely on stoichiometric strong oxidants or highly elect…
View article: Photoredox‐Catalyzed Decarboxylative Bromination, Chlorination and Thiocyanation Using Inorganic Salts
Photoredox‐Catalyzed Decarboxylative Bromination, Chlorination and Thiocyanation Using Inorganic Salts Open
Decarboxylative halogenation reactions of alkyl carboxylic acids are highly valuable reactions for the synthesis of structurally diverse alkyl halides. However, many reported protocols rely on stoichiometric strong oxidants or highly elect…
View article: Iridium-Catalyzed Asymmetric Difunctionalization of C–C σ-Bonds Enabled by Ring-Strained Boronate Complexes
Iridium-Catalyzed Asymmetric Difunctionalization of C–C σ-Bonds Enabled by Ring-Strained Boronate Complexes Open
Enantioenriched organoboron intermediates are important building blocks in organic synthesis and drug discovery. Recently, transition metal-catalyzed enantioselective 1,2-metalate rearrangements of alkenylboronates have emerged as an attra…
View article: Copper-Mediated Dehydrogenative C(sp<sup>3</sup>)–H Borylation of Alkanes
Copper-Mediated Dehydrogenative C(sp<sup>3</sup>)–H Borylation of Alkanes Open
Borylations of inert carbon-hydrogen bonds are highly useful for transforming feedstock chemicals into versatile organoboron reagents. Catalysis of these reactions has historically relied on precious-metal complexes, which promote dehydrog…
View article: De Novo Synthesis of Dihydrobenzofurans and Indolines and Its Application to a Modular, Asymmetric Synthesis of Beraprost
De Novo Synthesis of Dihydrobenzofurans and Indolines and Its Application to a Modular, Asymmetric Synthesis of Beraprost Open
Dihydrobenzofurans and indolines are important constituents of pharmaceuticals. Herein, we describe a novel strategy for their construction in which the aromatic ring is created de novo through an inverse-electron demand Diels-Alder…