David J. France

ORCID: 0000-0002-5409-3316
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About
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Research Areas
  • Catalytic C–H Functionalization Methods
  • Chemical Synthesis and Analysis
  • Catalytic Alkyne Reactions
  • Catalytic Cross-Coupling Reactions
  • Synthetic Organic Chemistry Methods
  • Carbohydrate Chemistry and Synthesis
  • Traditional and Medicinal Uses of Annonaceae
  • X-ray Diffraction in Crystallography
  • Crystallization and Solubility Studies
  • Cultural Heritage Materials Analysis
  • Cyclopropane Reaction Mechanisms
  • Cholinesterase and Neurodegenerative Diseases
  • Chemical synthesis and alkaloids
  • Microbial Natural Products and Biosynthesis
  • Crystallography and molecular interactions
  • Asymmetric Synthesis and Catalysis
  • Building materials and conservation
  • Dyeing and Modifying Textile Fibers
  • Antimicrobial Peptides and Activities
  • HIV/AIDS drug development and treatment
  • Molecular spectroscopy and chirality
  • Nanocluster Synthesis and Applications
  • Ocular Infections and Treatments
  • Genetic and Kidney Cyst Diseases
  • Advanced Chemical Sensor Technologies

University of Glasgow
2014-2024

Glasgow Life
2020

University of Cape Coast
2018

University of California, Irvine
2010-2012

University of Cambridge
2010-2011

Irvine University
2010

The Ohio State University
2003

The first total synthesis of (+)-sieboldine A was completed in 20 steps from readily available (3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (5). Key are as follows: (a) a pinacol-terminated 1,6-enyne cyclization reaction to form the cis-hydrindanone core (11 → 12), (b) formation spiro tetrahydrofuran ring by stereoselective DMDO oxidation tricyclic dihydropyran intermediate 15, and (c) unprecedented N-hydroxyazacyclononane thioglycoside precursor (18 19).

10.1021/ja103666n article EN Journal of the American Chemical Society 2010-05-19

Two is better that one: A new organocatalytic route for the asymmetric preparation of embedded piperazic acids and a Stille coupling an ortho-chloropyrroloindole served as key steps in total synthesis dimeric cyclopeptide chloptosin (see structure). Detailed facts importance to specialist readers are published "Supporting Information". Such documents peer-reviewed, but not copy-edited or typeset. They made available submitted by authors. Please note: The publisher responsible content...

10.1002/anie.201002880 article EN Angewandte Chemie International Edition 2010-07-19

This article describes synthetic studies that culminated in the first total synthesis of Lycopodium alkaloid sieboldine A. During this study, a number pinacol-terminated cationic cyclizations were examined to form cis-hydrindanone core Of these, mild Au(I)-promoted 1,6-enyne cyclization was terminated by semipinacol rearrangement proved be most efficient. Fashioning unprecedented N-hydroxyazacyclononane ring embedded within bicyclo[5.2.1]decane-N,O-acetal moiety A formidable challenge....

10.1021/jo300872y article EN The Journal of Organic Chemistry 2012-06-26

A palladium-catalyzed difunctionalization of unactivated alkenes with tethered nucleophiles is reported. The versatile reaction occurs simple allylic halides and can be carried out under air. methodology provides rapid access to a wide array desirable heterocyclic targets, as illustrated by concise synthesis the widely prescribed antidepressantcitalopram.

10.1039/c3sc51222c article EN cc-by Chemical Science 2013-01-01

Gigahertz- to terahertz-frequency infrared and Raman spectra contain a wealth of information concerning the structure, intermolecular forces, dynamics ionic liquids. However, these generally have large number contributions ranging from slow diffusional modes underdamped librations intramolecular vibrational modes. This makes it difficult isolate effects such as role Coulombic hydrogen-bonding interactions. We applied far-infrared ultrafast optical Kerr effect spectroscopies on carefully...

10.1021/jacs.7b03036 article EN cc-by Journal of the American Chemical Society 2017-05-17

Abstract Here we describe in full our investigations into the synthesis of dimeric cyclohexapeptide chloptosin 17 linear steps. Particularly, this work features an organocatalytic tandem process for embedded piperazic acids, which a differentially protected azodicarboxylate is used together with pyrrolidinyl tetrazole as catalyst. The central biaryl bond being formed by Stille coupling two sterically demanding ortho ‐chloropyrroloindole fragments. inherent flexibility synthetic strategy...

10.1002/chem.201003216 article EN Chemistry - A European Journal 2011-03-15

Reversible S-palmitoylation of protein cysteines, catalysed by a family integral membrane zDHHC-motif containing palmitoyl acyl transferases (zDHHC-PATs), controls the localisation, activity, and interactions numerous peripheral proteins. There are compelling reasons to want inhibit activity individual zDHHC-PATs in both laboratory clinic, but specificity existing tools is poor. Given extensive conservation zDHHC-PAT active site, development isoform-specific competitive inhibitors highly...

10.1371/journal.pone.0299665 article EN cc-by PLoS ONE 2024-03-21

Abstract Heterocycles are some of the most important and widely used motifs in synthetic medicinal chemistry. It is therefore not surprising that synthesis heterocycles a rich area chemical research. Catalytic heterocyclization makes use heteroatomic nucleophiles, such as oxygen nitrogen, one powerful strategy. This Focus Review considers an alternative approach uses carbon‐based nucleophiles generated during palladium‐catalyzed reactions. complimentary method allows access to range useful...

10.1002/ajoc.201600410 article EN Asian Journal of Organic Chemistry 2016-10-13

Doppelt gemoppelt: Ein neues organokatalytisches asymmetrisches Verfahren zum Aufbau der Piperazinsäure-Einheiten und die Stille-Kupplung eines ortho-Chlorpyrroloindols dienten in Totalsynthese des dimeren Cyclopeptids Chloptosin (siehe Struktur) als Schlüsselschritte. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents peer-reviewed, but not copy-edited or typeset. They made available submitted by the authors. Please note: The...

10.1002/ange.201002880 article EN Angewandte Chemie 2010-07-19

The contamination of ophthalmic solutions in practices remains an important cause a myriad secondary eye infections and source aggravation ocular disorders such as corneal ulcers keratitis. aim this study was to investigate the possible microbial fluorescein sodium dye used clinics Ghana.Fluorescein were collected from various Ghana. Twenty-one samples multiple-use regions Eighteen unopened bottles yet be also serve controls same facilities. inoculated different culture plates (blood agar,...

10.1111/cxo.12821 article EN Clinical and Experimental Optometry 2018-07-30

Cucurbiturils (CBs), barrel-shaped macrocyclic molecules, are capable of self-assembling at the surface nanomaterials in their native state, via carbonyl-ringed portals. However, symmetrical two-portal structure typically leads to aggregated nanomaterials. We demonstrate that fluorescent quantum dot (QD) aggregates linked with CBs can be broken-up, retaining adsorbed surface, inclusion guests CB cavity. Simultaneously, QD is modified by a functional tail on guest, thus high affinity...

10.1021/acsnano.3c06601 article EN cc-by ACS Nano 2023-11-03

Abstract Cross‐coupling reactions catalyzed by transition metals are among the most influential in modern synthetic chemistry. The vast majority of transition‐metal‐catalyzed cross‐couplings rely on a catalytic cycle involving alternating oxidation and reduction metal center generally limited to forging just one type new bond per reaction (e.g., biaryl linkage formed during Suzuki cross‐coupling). This work presents an Isohypsic‐Redox Sequence (IRS) that uses effect two cycles, thereby...

10.1002/chem.201804131 article EN cc-by Chemistry - A European Journal 2018-09-11

Infection by parasitic nematodes is widespread in the developing world causing extensive morbidity and mortality. Furthermore, infection of animals a global problem, with substantial impact on food production. Here we identify small molecule inhibitors nematode-specific metalloprotease, DPY-31, using both known metalloprotease virtual screening. This strategy successfully identified several μM DPY-31 from human filarial nematode Brugia malayi, gastrointestinal sheep Teladorsagia...

10.1016/j.bmcl.2015.10.077 article EN cc-by Bioorganic & Medicinal Chemistry Letters 2015-11-04

Furious furans: A recent article by Wang et al. reports a novel palladium-catalyzed cross-coupling reaction to form 2-alkenyl substituted furans from ene-yne-ketones. The electrophiles used in this study were benzyl, aryl and allyl bromides yield highly moderate good yields. palladium (2-furyl)carbene is proposed as key reactive intermediate, which supported DFT calculations.

10.1002/cctc.201301050 article EN ChemCatChem 2014-02-12

ADVERTISEMENT RETURN TO ISSUEPREVLetterNEXTConversion of the Enantiomers Spiro[4.4]nonane-1,6-Diol into Both Epimeric Carbaspironucleosides Having Natural C1' Absolute ConfigurationLeo A. Paquette, Ryan E. Hartung, and David J. FranceView Author Information Department Chemistry, Evans Chemical Laboratories, The Ohio State University, Columbus, 43210 Cite this: Org. Lett. 2003, 5, 6, 869–871Publication Date (Web):February 26, 2003Publication History Received2 January 2003Published online26...

10.1021/ol0340033 article EN Organic Letters 2003-02-26

Finding new methods of carbon–carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because their inherently nonplanar shape, forming sp3-rich scaffolds are particular importance. Although there combining heterocyclization and sp3–sp3 bonds, these form the carbon–heteroatom rather than heterocycle. Here, we show alkene arylallylation reaction that generates with concomitant two bonds. Furthermore, demonstrate this process occurs through an isohypsic...

10.1021/acsomega.8b01021 article EN cc-by ACS Omega 2018-07-31

Heritage conservation science is a valuable technique for improving understanding and the preservation of historical objects. Material analysis heritage textiles related materials provides information about polymer colorant degradation, contributes to improved display practices. The re‐creation following processes useful testing analytical techniques in field where ethical constraints often limit sampling, also identify potential age‐related changes relative fresh product. Despite broad...

10.1111/cote.12343 article EN Coloration Technology 2018-05-28

In this research, printed Turkey red calico from the 19th century is analysed using conservation-based techniques to identify materials used in their manufacture. production was a significant industry Scotland, and textiles found archives collections are valuable part of Scottish heritage material history. prints were produced via unique dyeing process followed by discharge printing, analysis paper SEM-EDX, FTIR, UHPLC, microscopy confirms they made as documented literature. Here, we show...

10.14568/cp2018019 article EN cc-by-nc-nd Conservar Património 2019-02-03

PF74 is a capsid-targeting inhibitor of HIV replication that effectively perturbs the highly sensitive viral uncoating process. A lack information regarding optical purity (enantiomeric excess) single stereogenic centre has resulted in ambiguity as to potency different samples this compound. Herein described synthesis enantiomerically enriched (S)- and (R)-PF74 further enrichment (≥98%) using chiral HPLC resolution. The biological activities each enantiomer were then evaluated, which...

10.3390/molecules26133919 article EN cc-by Molecules 2021-06-26

Here we demonstrate the coupling of MIDA boronates to allylic electrophiles, including a new synthesis well-known COX inhibitor ibuprofen.

10.1039/d0ra03338c article EN cc-by RSC Advances 2020-01-01

Abstract The presented method affords a wide range of biologically relevant heterocyclic compounds.

10.1002/chin.201405093 article EN ChemInform 2014-01-16
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