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Back Cover: Formal Total Synthesis of Diazonamide A by Indole Oxidative Rearrangement (Chem. Eur. J. 31/2016) 下载免费PDF全文
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Henry Robinson Steven A. Oatley James E. Rowedder Pawel Slade Dr. Simon J. F. Macdonald Dr. Stephen P. Argent Prof. Dr. Jonathan D. Hirst Thomas McInally Prof. Dr. Christopher J. Moody 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(34):7678-7684
A late-stage functionalization of the aromatic ring in amino acid derivatives is described. The key step is a copper-catalysed diversification of a boronate ester by amination (Chan–Lam reaction) that can be carried out on a complex β-aryl-β-amino acid scaffold. This not only considerably extends the substrate scope of amination partners, but also delivers an array of potent and selective integrin inhibitors as potential treatment agents of idiopathic pulmonary fibrosis (IPF). This versatile chemical strategy, which is amenable to high-throughput-array protocols, allows the installation of pharmaceutically valuable heteroaromatic fragments at a late stage by direct coupling to NH heterocycles, leading to compounds with drug-like attributes. It thus constitutes a useful addition to the medicinal chemist's repertoire. 相似文献
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Synthesis and Intracellular Redox Cycling of Natural Quinones and Their Analogues and Identification of Indoleamine‐2,3‐dioxygenase (IDO) as Potential Target for Anticancer Activity 下载免费PDF全文
Christopher E. Blunt Dr. Canan Torcuk Dr. Yang Liu Dr. William Lewis Dr. David Siegel Prof. Dr. David Ross Prof. Dr. Christopher J. Moody 《Angewandte Chemie (International ed. in English)》2015,54(30):8740-8745
Natural quinones, often linked with cellular oxidation processes, exhibit pronounced biological activity. In particular, the structurally unique isothiazolonaphthoquinone aulosirazole, isolated from blue‐green alga, possesses selective antitumor cytotoxicity, although its mechanism of action is unknown. The first synthesis of aulosirazole uses a route centered upon a late‐stage regioselective Diels–Alder reaction. The structurally related natural product pronqodine A, an inhibitor of prostaglandin release, and analogues thereof, were also prepared for comparison. Biological evaluation of the compounds identified one potential target as the immunoregulatory enzyme indoleamine‐2,3‐dioxygenase (IDO). The isothiazoloquinones are also efficient substrates for the human quinone reductase NQO1, and undergo intracellular NQO1‐dependent redox cycling resulting in the generation of reactive oxygen species, and at lower doses have the potential to alter the ratio of intracellular oxidized to reduced pyridine nucleotides. 相似文献
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The total synthesis of the unusual 4-pyridone marine metabolite lodopyridone has been achieved by late stage manipulation of the related 4-pyrone. Key reactions include a Suzuki–Miyaura coupling to form the tetracyclic core and a modified Corey–Ganem–Gilman reaction to install the ethanolamide side-chain. 相似文献
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A procedure for the selective deprotection of p-methoxybenzyl ethers using catalytic amounts of DDQ and of sodium nitrite, with oxygen as the terminal oxidant, is reported. 相似文献
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Singular spectrum analysis has recently become an attractive tool in a broad range of applications. Its main mechanism of alternating between rank reduction and Hankel projection to produce an approximation to a particular component of the original time series, however, deserves further mathematical justification. One paramount question to ask is how good an approximation that such a straightforward apparatus can provide when comparing to the absolute optimal solution. This paper reexamines this issue by exploiting a natural parametrization of a general Hankel matrix via its Vandermonde factorization. Such a formulation makes it possible to recast the notion of singular spectrum analysis as a semi-linear least squares problem over a compact feasible set, whence global optimization techniques can be employed to find the absolute best approximation. This framework might not be immediately suitable for practical application because global optimization is expectedly more expensive, but it does provide a theoretical baseline for comparison. As such, our empirical results indicate that the simpler SSA algorithm usually is amazingly sufficient as a handy tool for constructing exploratory model. The more complicated global methods could be used as an alternative of rigorous affirmative procedure for verifying or assessing the quality of approximation. 相似文献
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Andrew S. Rowan Thomas S. Moody Roger M. Howard Toby J. Underwood Iain R. Miskelly Yanan He Bo Wang 《Tetrahedron: Asymmetry》2013,24(21-22):1369-1381
Libraries of highly enantioenriched secondary alcohols in both enantiomeric forms were synthesised by enzymatic reduction of their parent ketones using selectAZyme? carbonyl reductase (CRED) technology. Commercially available CREDs were able to reduce a range of substrate classes efficiently and with very high enantioselectivity. Matching substrate classes to small subsets of CREDs enabled the fast development of preparative bioreductions and the rapid generation of 100–1500 mg samples of chiral alcohols in typically >95% ee and the majority in ?99.0% ee. The conditions for small scale synthesis were then scaled up to 0.5 kg to deliver one of the chiral alcohols, (S)-1-(4-bromophenyl)-2-chloroethanol, in 99.8% ee and 91% isolated yield. 相似文献
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Daniele Giallombardo Adam C. Nevin William Lewis Christopher C. Nawrat Russell R.A. Kitson Christopher J. Moody 《Tetrahedron》2014
A synthesis of the naturally occurring xanthone toxyloxanthone B is described, in which the key step is the regioselective addition of a methyl salicylate to a substituted benzyne, followed by cyclization of the intermediate aryl anion to form the xanthone, the regiochemistry of the aryne addition being confirmed by X-ray crystallography. Subsequent introduction of the pyran ring by [3,3]-rearrangement and deprotection completed the synthesis. 相似文献