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15 items found (0 items not approved), displaying 1 to 10.[First/Prev] 1, 2 [Next/Last]

Instruments / Technical Area	Publication Details	Published
I04-1-Macromolecular Crystallography (fixed wavelength)	Synthesis of a thiazole library via an iridium-catalyzed sulfur ylide insertion reaction Storm Hassell-Hart , Elisa Speranzini , Sirihathai Srikwanjai , Euan Hossack , S. Mark Roe , Daren Fearon , Daniel Akinbosede , Stephen Hare , John Spencer Organic Letters 24, 7924 - 7927 DOI: 10.1021/acs.orglett.2c02996 Open Access Show Abstract ▼ Abstract: A library of thiazoles and selenothiazoles were synthesized via Ir-catalyzed ylide insertion chemistry. This process is a functional group, particularly heterocycle-substituent tolerant. This was applied to the synthesis of fanetizole, an anti-inflammatory drug, and a thiazole-containing drug fragment that binds to the peptidyl-tRNA hydrolase (Pth) in Neisseria gonorrheae bacteria.	Nov 2022
I02-Macromolecular Crystallography I04-Macromolecular Crystallography	From 1,4-disaccharide to 1,3-glycosyl carbasugar: Synthesis of a bespoke inhibitor of family GH99 endo-α-mannosidase Dan Lu , Sha Zhu , Lukasz F. Sobala , Ganeko Bernardo-Seisdedos , Oscar Millet , Yongmin Zhang , Jesus Jiménez-Barbero , Gideon J. Davies , Matthieu Sollogoub Organic Letters DOI: 10.1021/acs.orglett.8b03260 Diamond Proposal Number(s): [9948] Show Abstract ▼ Abstract: Understanding the enzyme reaction mechanism can lead to the design of enzyme inhibitors. A Claisen rearrangement was used to allow conversion of an α-1,4-disaccharide into an α-1,3-linked glycosyl carbasugar to target the endo-α-mannosidase from the GH99 glycosidase family, which, unusually, is believed to act through a 1,2-anhydrosugar “epoxide” intermediate. Using NMR and X-ray crystallography, it is shown that glucosyl carbasugar α-aziridines can act as reasonably potent endo-α-mannosidase inhibitors, likely by virtue of their shape mimicry and the interactions of the aziridine nitrogen with the conserved catalytic acid/base of the enzyme active site.	Nov 2018
I19-Small Molecule Single Crystal Diffraction	Access to a guanacastepene and cortistatin-related skeleton via ethynyl lactone ireland–claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diyl Oleksandr Zhurakovskyi , Sam R. Ellis , Amber Thompson , Jeremy Robertson Organic Letters DOI: 10.1021/acs.orglett.7b00834 Diamond Proposal Number(s): [7768] Show Abstract ▼ Abstract: Heating a 2,5-furanocyclic (2-azidoethyl)allene initiates a cascade reaction comprising azide–allene cycloaddition, loss of nitrogen, and azatrimethylenemethane (ATMM) diyl–furan transannular (4 + 3)-cycloaddition. The major product of this reaction contains the pentacyclic core common to guanacastepenes D and H and radianspenes J–L; in addition, the central oxa-bridged cycloheptene ring, flanked by two carbocyclic rings, is structurally related to the ABC-ring system found in the cortistatins. This is the first reported synthetic application of a “free” (nonconjugated) ATMM. The cyclization precursors were prepared via the first reported examples of the Ireland–Claisen rearrangement of an ethynyl lactone.	Apr 2017
I19-Small Molecule Single Crystal Diffraction	Porphyrin–polyyne [3]- and [5]rotaxanes Daniel R. Kohn , Levon D. Movsisyan , Amber L. Thompson , Harry L. Anderson Organic Letters DOI: 10.1021/acs.orglett.6b03528 Diamond Proposal Number(s): [9981] Open Access Show Abstract ▼ Abstract: Porphyrin–polyyne [3]- and [5]rotaxanes have been synthesized by condensing aldehyde–rotaxanes with pyrrole or dipyrromethane. The crystal structure of a [3]rotaxane shows that the macrocycles adopt compact conformations, holding the hexaynes near the porphyrin core, and that the phenanthroline units form intermolecular π-stacked dimers in the solid. Fluorescence spectra reveal singlet excited-state energy transfer from the threaded hexayne to the porphyrin, from the phenanthroline to the porphyrin, and from the phenanthroline to the hexayne.	Jan 2017
I19-Small Molecule Single Crystal Diffraction	Enantioselective synthesis of 4- and 6-azaindolines by a cation-directed cyclization Alan D. Lamb , Peter D. Davey , Russell W. Driver , Amber L. Thompson , Martin D. Smith Organic Letters 18, 5372 - 5375 DOI: 10.1021/acs.orglett.6b02744 Diamond Proposal Number(s): [7768] Open Access Show Abstract ▼ Abstract: Functionalized 4- and 6-azaindolines are accessible with high levels of enantioselectivity by the cation-directed cyclization of aminopyridine-derived imines via phase-transfer catalysis. The extension of this methodology to diastereoselective cyclizations is also described.	Oct 2016
I19-Small Molecule Single Crystal Diffraction	Regioswitchable palladium-catalyzed decarboxylative coupling of 1,3-dicarbonyl compounds Miles Kenny , Jeppe Christensen , Simon Coles , Vilius Franckevičius Organic Letters 17 (15), 3926 - 3929 DOI: 10.1021/acs.orglett.5b01979 Diamond Proposal Number(s): [8521, 11238] Show Abstract ▼ Abstract: A palladium-catalyzed chemo- and regioselective coupling of 1,3-dicarbonyl compounds via an allylic linker has been developed. This reaction, which displays broad substrate scope, forms two C–C bonds and installs two all-carbon quaternary centers. The regioselectivity of the reaction can be predictably controlled by utilizing an enol carbonate of one of the coupling partners.	Aug 2015
I19-Small Molecule Single Crystal Diffraction	Diastereoselective synthesis of fused lactone-pyrrolidinones; application to a formal synthesis of (-)-salinosporamide A Angus W. J. Logan , Simon J. Sprague , Robert W. Foster , Léo B. Marx , Vincenzo Garzya , Michal S. Hallside , Amber Thompson , Jonathan W. Burton Organic Letters 16 (16), 4078 - 4081 DOI: 10.1021/ol501662t Diamond Proposal Number(s): [7768] Open Access Show Abstract ▼ Abstract: A mild, diastereoselective synthesis of fused lactone-pyrrolidinones using an oxidative radical cyclization is reported. The methodology is demonstrated in a formal synthesis of (−)-salinosporamide A.	Aug 2014
I19-Small Molecule Single Crystal Diffraction	Triptycene-based organic molecules of intrinsic microporosity Rupert G. D. Taylor , Mariolino Carta , C. Grazia Bezzu , Jonathan Walker , Kadhum J. Msayib , Benson M. Kariuki , Neil B. Mckeown Organic Letters 16 (7), 1848 - 1851 DOI: 10.1021/ol500591q Diamond Proposal Number(s): [7598] Open Access Show Abstract ▼ Abstract: Four Organic Molecules of Intrinsic Microporosity (OMIMs) were prepared by fusing triptycene-based components to a biphenyl core. Due to their rigid molecular structures that cannot pack space efficiently, these OMIMs form amorphous materials with significant microporosity as demonstrated by apparent BET surface areas in the range of 515–702 m2 g–1. Bulky cyclic 1′,2′,3′,4′-tetrahydro-1′,1′,4′,4′-tetramethylbenzo units placed on the triptycene termini are especially efficient at enhancing microporosity.	Apr 2014
I19-Small Molecule Single Crystal Diffraction	(−)-(2S,3R,Z)-nakinadine A: first asymmetric synthesis and absolute configuration assignment Stephen G. Davies , Ai Fletcher , Paul M. Roberts , Rushabh S. Shah , Amber Thompson , James E. Thomson Organic Letters 16 (5), 1354 - 1357 DOI: 10.1021/ol500096r Show Abstract ▼ Abstract: Mannich-type reaction of methyl phenylacetate with the N-tert-butylsulfinyl imine derived from (R)-tert-butylsulfinamide and (Z)-14-(pyridin-3′-yl)tetradec-11-enal has been used as the key step in the first asymmetric synthesis of (−)-nakinadine A. Both the 2,3-syn- and 2,3-anti-diastereoisomers were prepared; comparison of spectroscopic and specific rotation data facilitated assignment of the absolute (2S,3R,Z)-configuration within the natural product. (−)-(2S,3R,Z)-Nakinadine A was prepared in 10 steps from 11-bromoundecan-1-ol, in 10% overall yield, 97:3 dr [(Z):(E) ratio], and >98% ee.	Mar 2014
I19-Small Molecule Single Crystal Diffraction	Tethered aminohydroxylation: synthesis of the β-amino acid of microsclerodermins A and B Robert D. C. Pullin , Akshat H. Rathi , Ekaterina Y. Melikhova , Christian Winter , Amber L. Thompson , Timothy J. Donohoe Organic Letters 15 (21) DOI: 10.1021/ol402638n Open Access Show Abstract ▼ Abstract: The utility of the tethered aminohydroxylation (TA) has been demonstrated by synthesis of the complex â-amino acid residue of microsclerodermins A and B. The TA provided a regio- and tereoselective functionalization of a complex homoallylic alcohol. The route includes latestage introduction of the aliphatic side chain via a cuprate addition and cross metathesis, a tactic designed to render the synthesis applicable to other microsclerodermins.	Oct 2013

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