Australian Journal of Chemistry Australian Journal of Chemistry Society
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Australian Journal of Chemistry

Australian Journal of Chemistry

Volume 68 Number 12 2015



Richard J. Payne and Craig A. Hutton
pp. 1789-1790
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In April 2015, the third instalment of the biennial SynthCon meeting, SynthCon3, was held at Fergusson's Winery in the Yarra Valley. This Research Front showcases the latest developments in synthetic organic chemistry research from the meeting.

CH15389Brønsted Acid-Mediated Radical Processes in Organic Synthesis

Thomas P. Nicholls, Luke C. Henderson and Alex C. Bissember
pp. 1791-1795
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This highlight focuses on applications of Brønsted acid-mediated radical processes across a range of reaction manifolds. A brief overview of significant research developments in the area and a discussion of the key mechanistic features of notable transformations are provided.

CH15397Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst

Steven-Alan G. Abel, Wesley J. Olivier, Richard L. Pederson, Alex C. Bissember and Jason A. Smith
pp. 1815-1820
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(R)-Harmonine was synthesised in 15 % overall yield via a six-step sequence exploiting a Z-selective cross-metathesis reaction as its centrepiece. By this strategy, the cis-olefin present in the target could be installed exclusively. This method was also used to prepare two novel analogues of harmonine.

CH15407Studies Towards a Concise Enantioselective Synthesis of Roseophilins

Daniel J. Kerr and Bernard L. Flynn
pp. 1821-1828
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An oxazolidone auxiliary-controlled asymmetric Nazarov reaction has been applied to the synthesis of the cyclopentyl-fused pyrrole core of the roseophilins, and a concise synthetic route to the pyrrole-furan biaryl fragment required in the synthesis of dechlororoseophilin is described. It is anticipated that these two syntheses can be combined in future efforts to provide efficient, convergent access to (+)-dechlororoseophilin.

CH15461The Synthesis and Biological Evaluation of Anithiactin A/Thiasporine C and Analogues

Richard A. Lamb, Michael P. Badart, Brooke E. Swaney, Sinan Gai, Sarah K. Baird and Bill C. Hawkins
pp. 1829-1833
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The synthesis of anithiactin A has been achieved in four steps. Several closely related analogues were synthesised and their biological activity against colon and breast cancer cell lines evaluated. Anithiactin A was found to not be cytotoxic even at a high concentration (100 μM); however, two 4-substituted phenyl thiazoles were found to be moderately cytotoxic at 10 μM.

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Galanthamine and codeine are reported to be positive allosteric modulators of nicotinic acetylcholine receptors (nAChRs), but their binding sites are not well defined. Thiol-reactive probes that are suitable for covalent trapping, an extension of the substituted cysteine accessibility method, are prepared to elucidate the allosteric binding sites of galanthamine and codeine at nAChRs.

CH15504Steric and Electronic Effects in the Synthesis and Regioselective Hydrolysis of Unsymmetrical Imides

Jing Shang, Aysa Pourvali, James R. Cochrane and Craig A. Hutton
pp. 1854-1858
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The AgI-promoted coupling reaction of thioamides and carboxylic acids is shown to be a useful method for the generation of unsymmetrical imides, which can then be converted into amides or other carboxylic acid derivatives. An interplay of both steric and electronic effects is observed in both the imide formation and subsequent solvolysis, allowing for optimization of yield and control of regioselectivity.

CH15465Synthesis of Non-Symmetrical and Atropisomeric Dibenzo[1,3]diazepines: Pd/CPhos-Catalysed Direct Arylation of Bis-Aryl Aminals

Tim Wezeman, Yuling Hu, John McMurtrie, Stefan Bräse and Kye-Simeon Masters
pp. 1859-1865
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Pd/CPhos-catalysis provides direct arylation/cyclisation of methylene-linked bis-anilines to dibenzo[1,3]diazepines, which are both non-(C2)-symmetrical and axially chiral. The cyclic targets are formed by heating (ortho-halo)aryl-aminal-linked arenes and potassium carbonate in dimethylacetamide in the presence of palladium acetate and CPhos. This method appears to be the first reported for the synthesis of this class of heterocycles in a C1-(a)symmetric manner.

CH15587Unexpected Isomerisation of a Fragment Analogue During Fragment-Based Screening of HIV Integrase Catalytic Core Domain

John H. Ryan, Karen E. Jarvis, Roger J. Mulder, Craig L. Francis, G. Paul Savage, Olan Dolezal, Thomas S. Peat and John J. Deadman
pp. 1871-1879
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Fragment-based screening of human immunodeficiency virus type 1 (HIV) integrase revealed a hit analogue that bound in an isomerised form to the LEDGF binding site. The starting lactone was stable in CDCl3; however, it unexpectedly isomerised in [D6]DMSO to give the same carboxylic acid as that found in the LEDGF binding site.

CH15434Synthesis and Properties of Photoswitchable Carbohydrate Fluorosurfactants

Yingxue Hu, Joshua B. Marlow, Rajesh Ramanathan, Wenyue Zou, Hui Geok Tiew, Matthew J. Pottage, Vipul Bansal, Rico F. Tabor and Brendan L. Wilkinson
pp. 1880-1884
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A new family of photoswitchable carbohydrate fluorosurfactant is described. Novel fluorosurfactants were synthesised using the copper(i)-catalysed azide–alkyne cycloaddition reaction and were isolated in moderate to high yields. These materials displayed unusual photocontrollable surface tension and selective antibacterial activity that was dependent on the carbohydrate and regiochemistry of the fluoroalkyl group.

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Efforts toward the total synthesis and stereochemical assignment of the cyclic depsipeptide natural product microspinosamide are described. A native chemical ligation–oxidation sequence was used to assemble a potential diastereoisomer from two fragments, a cyclic depsipeptide and a linear peptide thioester.

CH15079Investigation of the Effects of Various Cyclodextrins on the Stabilisation of Human Serum Albumin by a Spectroscopic Method

Mohsen Oftadeh, Golamreza Rezaei Behbahani, Ali Akbar Saboury and Shahnaz Rafiei
pp. 1894-1899
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The binding parameters between cyclodextrins (CDs) and human serum albumin (HSA) were investigated. The obtained heats for HSA+CDs interactions were reported and analysed in terms of the extended solvation model. The binding constants and thermodynamic parameters were obtained.

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Three kinds of Mn-containing perovskites La0.8MnO3–δ, LaMnO3+δ and LaMn0.8O3–δ have been investigated for ethanol deep oxidation in the temperature range 100–300°C. La0.8MnO3-δ shows the best catalytic activity, due to its low surface basicity (lowest La/Mn ratio) and high redox properties (highest Mn4+/Mn3+ ratio).

CH15154Improving Cycling Performance of LiMn2O4 Battery by Adding an Ester-Functionalized Ionic Liquid to Electrolyte

Tao Dong, Suojiang Zhang, Liang Zhang, Shimou Chen and Xingmei Lu
pp. 1911-1917
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LiMn2O4 has attracted great attention because of its excellent merits for application in lithium-ion batteries. However, it suffers from rapid capacity fading during electrochemical cycling. In this article, N-methylpyrrolidinium-N-acetate bis(trifluoromethylsulfonyl)imide was designed as an additive to electrolyte for improving the electrochemical performance of Li/LiMn2O4 half-cells.

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Professor Kenneth Seddon OBE, one of AJC’s longest-standing Editors, sadly passed away on 21 January from prostate cancer. Ken was one of the world's best ionic liquids experts. His consistent unwavering support, loyalty and advocacy for AJC over the last 10 years will be sorely missed.