Richmond Sarpong
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View article: Methylglyoxal-induced glycation stress promotes aortic stiffening: putative mechanistic roles of oxidative stress and cellular senescence
Methylglyoxal-induced glycation stress promotes aortic stiffening: putative mechanistic roles of oxidative stress and cellular senescence Open
MGO-induced glycation stress contributes to aortic stiffening and glycation stress lowering compounds hold promise for mitigating these effects.
View article: Total synthesis and biological activity of "carbamorphine": O-to-CH2 replacement in the E-ring of the morphine core structure.
Total synthesis and biological activity of "carbamorphine": O-to-CH2 replacement in the E-ring of the morphine core structure. Open
Morphine is a µ-opioid receptor (MOR) agonist and potent analgesic. However, it displays several side effects including respiratory depression and addiction. Here, we show that a single heavy atom replacement in the morphine core structure…
View article: Total synthesis and biological activity of “carbamorphine”: O-to-CH <sub>2</sub> replacement in the E-ring of the morphine core structure
Total synthesis and biological activity of “carbamorphine”: O-to-CH <sub>2</sub> replacement in the E-ring of the morphine core structure Open
Morphine is a µ-opioid receptor (MOR) agonist and potent analgesic. However, it displays several side effects including respiratory depression and addiction. Here, we show that a single heavy atom replacement in the morphine core structure…
View article: Benchmarking Snow Fields of ERA5-Land in the Northern Regions of North America
Benchmarking Snow Fields of ERA5-Land in the Northern Regions of North America Open
Reanalysis products provide new opportunities for assessments of historical Earth System states. This is crucial for snow variables, where ground-based observations are sparse and incomplete, and remote sensing measurements still face limi…
View article: Phototransposition of Indazoles to Benzimidazoles: Tautomer‐Dependent Reactivity, Wavelength Dependence, and Continuous Flow Studies
Phototransposition of Indazoles to Benzimidazoles: Tautomer‐Dependent Reactivity, Wavelength Dependence, and Continuous Flow Studies Open
Herein, we report a detailed investigation of the photomediated transformation of indazoles to benzimidazoles through a nitrogen–carbon transposition. This phototransposition is known to occur in low yield when 1 H ‐indazoles are subjected…
View article: Two-Step Constitutional Isomerization of Saturated Cyclic Amines Using Borane Catalysis
Two-Step Constitutional Isomerization of Saturated Cyclic Amines Using Borane Catalysis Open
The prevalence of saturated azacycles within pharmaceuticals, natural products, and agrochemicals has prompted the development of many methods that modify their periphery. In contrast, technologies that interconvert distinct saturated azac…
View article: Methylglyoxal-induced glycation stress promotes aortic stiffening: Putative mechanistic roles of oxidative stress and cellular senescence
Methylglyoxal-induced glycation stress promotes aortic stiffening: Putative mechanistic roles of oxidative stress and cellular senescence Open
Background Here, we assessed the role of the advanced glycation end-product (AGE) precursor methylglyoxal (MGO) and its non-crosslinking AGE MGO-derived hydroimidazolone (MGH)-1 in aortic stiffening and explored the potential of a glycatio…
View article: Interrogation of Enantioselectivity in the Photomediated Ring Contractions of Saturated Heterocycles
Interrogation of Enantioselectivity in the Photomediated Ring Contractions of Saturated Heterocycles Open
We recently reported a chiral phosphoric acid (CPA) catalyzed enantioselective photomediated ring contraction of piperidines and other saturated heterocycles. By extruding a single heteroatom from a ring, this transformation builds desirab…
View article: Cheminformatic Analysis of Core-Atom Transformations in Pharmaceutically Relevant Heteroaromatics
Cheminformatic Analysis of Core-Atom Transformations in Pharmaceutically Relevant Heteroaromatics Open
Heteroaromatics are the basis for many pharmaceuticals. The ability to modify these structures through selective core-atom transformations, or "skeletal edits", can dramatically expand the landscape for drug discovery and development. Howe…
View article: Reductive Amination of Carbonyl C–C Bonds Enables Formal Nitrogen Insertion
Reductive Amination of Carbonyl C–C Bonds Enables Formal Nitrogen Insertion Open
Given its relevance across numerous fields, reductive amination is one of the oldest and most widely used methods for amine synthesis. As a cornerstone of synthetic chemistry, it has largely remained unchanged since its discovery over a ce…
View article: C–H functionalization of camphor through emerging approaches
C–H functionalization of camphor through emerging approaches Open
Camphor and related monoterpenoid natural products have served as versatile “chiral pool” materials in organic chemistry for over half a century. Historically, many researchers have used a variety of transformations involving orchestrated …
View article: Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of α-Pinene
Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of α-Pinene Open
The development of several unique strategies and tactics for the synthesis of α-pinene isotopologues that has culminated in access to all eight possible isomers with deuterium incorporated selectively at each available carbon atom is descr…
View article: Molecular complexity as a driving force for the advancement of organic synthesis
Molecular complexity as a driving force for the advancement of organic synthesis Open
View article: Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of a-Pinene
Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of a-Pinene Open
The development of several unique strategies and tactics for the synthesis of a-pinene isotopologues that has culminated in access to all eight possible isomers with deuterium incorporated selectively at each available carbon atom is descr…
View article: Reductive amination of carbonyl C–C bonds enables formal nitrogen insertion
Reductive amination of carbonyl C–C bonds enables formal nitrogen insertion Open
Given its ubiquity in various biological and physical processes1–3, the reductive amination of ketones and aldehydes is one of the oldest and most widely used methods for amine synthesis4. As a cornerstone of synthetic chemistry, it has la…
View article: Total Synthesis of (±)‐Baphicacanthcusine A Enabled by Sequential Ring Contractions
Total Synthesis of (±)‐Baphicacanthcusine A Enabled by Sequential Ring Contractions Open
Reported herein is the first total synthesis of the poly ‐pseudoindoxyl natural product baphicacanthcusine A. The synthesis leverages the oxidative rearrangement of indoles to pseudoindoxyls to install vicinal pseudoindoxyl heterocycles in…
View article: Late-stage benzenoid-to-troponoid skeletal modification of the cephalotanes exemplified by the total synthesis of harringtonolide
Late-stage benzenoid-to-troponoid skeletal modification of the cephalotanes exemplified by the total synthesis of harringtonolide Open
Skeletal modifications enable elegant and rapid access to various derivatives of a compound that would otherwise be difficult to prepare. They are therefore a powerful tool, especially in the synthesis of natural products or drug discovery…
View article: Construction of Seven-Membered Oxacycles Using a Rh(I)-Catalyzed Cascade C–C Formation/Cleavage of Cyclobutenol Derivatives
Construction of Seven-Membered Oxacycles Using a Rh(I)-Catalyzed Cascade C–C Formation/Cleavage of Cyclobutenol Derivatives Open
Herein, we describe the synthesis of substituted oxepane derivatives through the skeletal remodeling of 4-hydroxy-2-cyclobutenones, which are readily prepared from commercially available dialkyl squarates upon their reaction with acrylonit…
View article: An attempted oxidative coupling approach to the scholarinine A framework
An attempted oxidative coupling approach to the scholarinine A framework Open
View article: Mechanistic Investigation, Wavelength-Dependent Reactivity, and Expanded Reactivity of <i>N</i>–Aryl Azacycle Photomediated Ring Contractions
Mechanistic Investigation, Wavelength-Dependent Reactivity, and Expanded Reactivity of <i>N</i>–Aryl Azacycle Photomediated Ring Contractions Open
Under mild blue-light irradiation, α-acylated saturated heterocycles undergo a photomediated one-atom ring contraction that extrudes a heteroatom from the cyclic core. However, for nitrogenous heterocycles, this powerful skeletal edit has …
View article: Late-Stage “Benzenoid-to-Troponoid” Skeletal Modification of the Cephalotanes: Total Synthesis of Harringtonolide and Computational Analysis
Late-Stage “Benzenoid-to-Troponoid” Skeletal Modification of the Cephalotanes: Total Synthesis of Harringtonolide and Computational Analysis Open
Inspired by the biosynthesis of the cephalotane natural products, we envisioned that a “single-atom insertion” into the framework of the benzenoid subfamily would provide access to the troponoid congeners — representing the reverse of the …
View article: CCDC 2297677: Experimental Crystal Structure Determination
CCDC 2297677: 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: CCDC 2297675: Experimental Crystal Structure Determination
CCDC 2297675: 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: CCDC 2297673: Experimental Crystal Structure Determination
CCDC 2297673: 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: CCDC 2297674: Experimental Crystal Structure Determination
CCDC 2297674: 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: CCDC 2297678: Experimental Crystal Structure Determination
CCDC 2297678: 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: CCDC 2306174: Experimental Crystal Structure Determination
CCDC 2306174: 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: CCDC 2297676: Experimental Crystal Structure Determination
CCDC 2297676: 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: Navigating Excess Complexity: Total Synthesis of Daphenylline
Navigating Excess Complexity: Total Synthesis of Daphenylline Open
Retrosynthetic analysis is a framework for designing synthetic routes to complex molecules that generally prioritizes disconnections which reduce molecular complexity. However, strict adherence to this principle can overlook pathways invol…
View article: Correction: Convergent synthesis of thiodiazole dioxides from simple ketones and amines through an unusual nitrogen-migration mechanism
Correction: Convergent synthesis of thiodiazole dioxides from simple ketones and amines through an unusual nitrogen-migration mechanism Open
Correction for ‘Convergent synthesis of thiodiazole dioxides from simple ketones and amines through an unusual nitrogen-migration mechanism’ by Kunlayanee Punjajom et al. , Chem. Sci. , 2024, 15 , 328–335, https://doi.org/10.1039/D3SC04478…