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William J. Coates

Bio: William J. Coates is an academic researcher from GlaxoSmithKline. The author has contributed to research in topics: Isomerization & Lewis acids and bases. The author has an hindex of 7, co-authored 10 publications receiving 168 citations. Previous affiliations of William J. Coates include University of Leeds & Imperial College London.

Papers
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TL;DR: The reaction of ring-closing metathesis-derived cyclic allylsiloxanes 3 with aldehydes in the presence of a Lewis acid gives 2,3,4-trisubstituted tetrahydrofurans related to the furanolignan family of natural products.
Abstract: The reaction of ring-closing metathesis-derived cyclic allylsiloxanes 3 with aldehydes in the presence of a Lewis acid gives 2,3,4-trisubstituted tetrahydrofurans related to the furanolignan family of natural products. The reactions proceed with complete 3,4-trans stereoselectivity, whereas the C-2 stereochemistry depends on both the aldehyde and Lewis acid used. When boron trifluoride etherate is used with aliphatic or electronically neutral aryl aldehydes, the reactions favor the production of the 2,3-cis isomer 8, whereas electron-rich aryl aldehydes lead to the 2,3-trans isomer 9 by Lewis acid-mediated isomerization of the kinetically favored cis isomer. The isomerization can be avoided by use of TMSOTf as a promoter, and hence, the stereochemistry can be tuned by appropriate choice of reagent. Cleavage of the pendant 3-ethenyl group installs the 3-hydroxymethyl group common to the furanolignans.

67 citations

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TL;DR: In this article, solid phase microwave-assisted RCM was used to synthesize 2, 3 and 4-carbon analogues of the natural disulfide and found to have Ki values against chymotrypsin in the low to sub-micromolar range.
Abstract: Bowman–Birk inhibitor analogues containing 2, 3 and 4-carbon analogues of the natural disulfide were synthesised via solid phase microwave-assisted RCM and found to have Ki values against chymotrypsin in the low to sub-micromolar range, the best replacement for the disulfide arising from the linkage by RCM of two L-homoallylglycine residues.

30 citations

Journal ArticleDOI
TL;DR: The trichloroacetates 2, 4 and 5, derived from the corresponding tryptophols, in methanolic acetonitrile results in photocyclisation to the indole 4position, and the formation of the pyrrolobenzoxocines as mentioned in this paper.
Abstract: Irradiation of the trichloroacetates 2, 4 and 5, derived from the corresponding tryptophols, in methanolic acetonitrile results In photocyclisation to the indole 4-position, and the formation of the pyrrolobenzoxocines 9–11. Attempted photocyclisation of the ‘reversed’α-chloro esters 15a, 15b and 18 was thwarted by readily occurring elimination of HCl, although the dimethyl compound 15c did cyclise to give the cycloheptaindole 20 upon irradiation in acetonitrile.

21 citations

Journal ArticleDOI
TL;DR: The discovery and optimization of a small molecule agonist and initial docking studies of this ligand into the receptor in order to provide a suitable lead and tool compound for the elucidation of the physiological function of the receptor.
Abstract: The novel 7-transmembrane receptor MrgX1 is located predominantly in the dorsal root ganglion and has consequently been implicated in the perception of pain. Here we describe the discovery and optimization of a small molecule agonist and initial docking studies of this ligand into the receptor in order to provide a suitable lead and tool compound for the elucidation of the physiological function of the receptor.

16 citations

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TL;DR: In this paper, it was shown that irradiation of N-chloroacetyl-tryptophan derivatives gives, after addition of a nucleophile in work-up, 7-substituted pyrrolobenzazocines with trans-stereospecificity.
Abstract: Although irradiation of N-chloroacetyltryptophan results in a poor yield of photocyclisation to the indole 4-position due to competing cyclisation to C-2, the photocyclisation of (dichloroacetyl)tryptophan derivatives gives, after addition of a nucleophile in work-up, 7-substituted pyrrolobenzazocines in good yield and with trans-stereospecificity. N-(Trichloroacetyl)tryptophan derivatives also undergo photocyclisation to give 3,4-bridged indoles. The structures of the azocinoindoles 13, 21, 22 and 35, and the azepinoindole 15 were confirmed by X-ray crystallography. In one case the preparation of a cycloalka[c, d]indole was possible by the irradiation of the α-chloro amide of an indol-3-yl alkanoic acid.

16 citations


Cited by
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Journal ArticleDOI
TL;DR: This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.
Abstract: Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of "microwave flash heating" in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

3,044 citations

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TL;DR: This review covers the important transformations that have been used in the stereoselective synthesis of tetrahydrofurans, with emphasis placed on literature published between 1993–2005.

263 citations

Journal ArticleDOI
Dong Liu1, Chao Liu1, Heng Li1, Aiwen Lei2, Aiwen Lei1 
TL;DR: This paper aims to demonstrate the efforts towards in-situ applicability of EMMARM, as to provide real-time information about concrete mechanical properties such as E-modulus and compressive strength.
Abstract: the 973 Program (2012CB725302);the National Natural Science Foundation of China (21025206;21272180);the China Postdoctoral Science Foundation funded project (2012M521458);the Program for Changjiang Scholars and Innovative Research Team in University (IRT1030)

252 citations

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TL;DR: In den vergangenen Jahren ist das Erhitzen and Beschleunigen chemischer Reaktionen durch Mikrowellenenergie popular geworden as discussed by the authors.
Abstract: Die offene Flamme konnte erst gezielt als Heizquelle fur Reaktionsgefase in der Synthesechemie verwendet werden, nachdem Robert Bunsen 1855 den nach ihm benannten Brenner erfunden hatte. Der Bunsen-Brenner wurde spater durch den Heizpilz, das Olbad und die Heizplatte als Warmequellen fur chemische Reaktionen abgelost. In den vergangenen Jahren ist das Erhitzen und Beschleunigen chemischer Reaktionen durch Mikrowellenenergie popular geworden. Diese Heiztechnik hat sich von einer Laborkuriositat zu einer etablierten Methode entwickelt, die an Universitaten und in der Industrie stark genutzt wird. Die effiziente Verringerung der Reaktionszeiten (von Tagen und Stunden auf Minuten und Sekunden) ist nur einer der vielen Vorteile des schnellen Erhitzens mit Mikrowellen (“microwave flash heating”). Dieser Aufsatz gibt einen Uberblick uber neuere Anwendungen des kontrollierten Mikrowellenerhitzens in der modernen organischen Synthese und diskutiert einige grundlegende Vorgange.

222 citations