ORCID Profile
0000-0001-5515-2878
Current Organisation
University of Tasmania
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Organic Chemical Synthesis | Organometallic Chemistry | Other Chemical Sciences | Analytical chemistry | Microfluidics and nanofluidics | Catalysis and Mechanisms of Reactions | Organometallic chemistry | Separation science | Quantum Chemistry | Theoretical and Computational Chemistry
Publisher: CSIRO Publishing
Date: 2015
DOI: 10.1071/CH15389
Abstract: This highlight focuses on recent applications of Brønsted acid-mediated radical processes across a range of reaction manifolds, including transition metal-based catalysis, photochemistry, and polymer science. A brief overview of significant research developments in the area and a discussion of the key mechanistic features of notable transformations are provided.
Publisher: American Chemical Society (ACS)
Date: 23-05-2018
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D2NP00058J
Abstract: The Stemona alkaloids represent a large and structurally- erse family of natural products. A selection of case studies are presented to showcase the key strategies and progress in the synthesis of these natural products since 2009.
Publisher: American Chemical Society (ACS)
Date: 30-12-2021
Publisher: American Chemical Society (ACS)
Date: 04-09-2019
DOI: 10.1021/JACS.9B08634
Abstract: Bench- and air-stable 1-methoxy-2,2,6,6-tetramethylpiperidine (TEMPO-Me) is relatively unreactive at ambient temperature in the absence of an electrochemical stimulus. In this report, we demonstrate that the one-electron electrochemical oxidation of TEMPO-Me produces a powerful electrophilic methylating agent in situ. Our computational and experimental studies are consistent with methylation proceeding via a S
Publisher: American Chemical Society (ACS)
Date: 05-2018
DOI: 10.1021/ACS.JNATPROD.7B01038
Abstract: Extensive phytochemical studies of the paleoendemic Tasmanian Proteaceae species Bellendena montana, Cenarrhenes nitida, and Persoonia gunnii were conducted employing pressurized hot water extraction. As part of these studies, six novel glycosides were isolated, including rare ex les of glycoside-containing natural products featuring tiglic acid esters. These polar molecules may represent potential phytochemical markers in ancient Proteaceae.
Publisher: American Chemical Society (ACS)
Date: 29-11-2007
DOI: 10.1021/OL7021774
Abstract: Treatment of the gem-dihalogenocyclopropanes 1-5 with potassium tert-butoxide or LDA results in the formation of the corresponding and annulated pyrroles 13-17, respectively.
Publisher: American Chemical Society (ACS)
Date: 18-12-2016
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C8DT04116D
Abstract: Novel bis(2,9-diaryl-1,10-phenanthroline)copper( i ) complexes were prepared to study a photoredox-catalysed reaction.
Publisher: American Chemical Society (ACS)
Date: 22-10-2021
DOI: 10.1021/ACS.ORGLETT.1C03205
Abstract: This report investigates the fundamental basis for rather surprising patterns of reactivity in Brønsted acid-mediated cyclizations of pyrrole substrates bearing pendant Michael acceptors that were identified during syntheses of
Publisher: Elsevier
Date: 2017
Publisher: American Chemical Society (ACS)
Date: 14-04-2021
Publisher: American Chemical Society (ACS)
Date: 17-02-2023
Publisher: Springer Science and Business Media LLC
Date: 09-03-2018
Publisher: Wiley
Date: 11-09-2019
DOI: 10.1111/AAS.13459
Abstract: The aetiology and risk factors for clinically important gastrointestinal bleeding (CIB) in adult ICU patients may differ according to the onset of CIB, which could affect the balance between benefits and harms of stress ulcer prophylaxis (SUP). We assessed the time to CIB in the Stress Ulcer Prophylaxis in the Intensive Care Unit (SUP-ICU) trial. We assessed if associations between baseline characteristics including allocation to SUP and CIB changed during time in the ICU, specifically in the later (after day 2) compared to the earlier (first 2 days) period, using Cox models adjusted for SAPS II and allocation to SUP. Additionally, we described baseline characteristics and CIB episodes stratified by earlier/later/no CIB and 90-day mortality status. Clinically important gastrointestinal bleeding occurred in 110/3291 (3.3%) patients after a median of 6 (interquartile range 2-13) days 25.5% of the episodes occurred early. Higher SAPS II was consistently associated with increased risk of CIB (hazard ratio (HR) 1.03, 95% confidence interval (CI) 1.01-1.05 in the earlier period vs HR 1.02, 95% CI 1.01-1.03 in the later period P = .37) university hospital admission was associated with decreased risk of earlier CIB (HR 0.30, 95% CI 0.14-0.63) this significantly increased in the later period (to HR 0.85, 95% CI 0.53-1.37 P = .02). Patients with later compared to earlier CIB received more transfusions and had more diagnostic/therapeutic procedures for CIB. Clinically important gastrointestinal bleeding mostly occurred more than 2 days after randomization. University hospital admission was associated with significantly decreased risk of CIB in the earlier period only.
Publisher: CSIRO Publishing
Date: 2018
DOI: 10.1071/CH18265
Abstract: Studies of the phytochemistry of carob (Ceratonia siliqua) leaf material are extremely limited. This report features the second natural product isolation study of carob leaves and the first such investigation of C. siliqua grown in Australia. Investigation of leaf material from seven carob cultivars using pressurised hot water extraction (PHWE) revealed the presence of high levels of myricitrin, d-pinitol, and sucrose in addition to the previously unreported natural product siliquapyranone {(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-(((2S,4S)-2-methyl-6-oxotetrahydro-2H-pyran-4-yl)oxy)tetrahydro-2H-pyran-3,4-diyl bis(3,4,5-trihydroxybenzoate)}. Siliquapyranone represents a biosynthetic fusion of conventional 2,3-gallate esters on a β-glucose tannin with a hydroxytetrahydro-2H-pyran-2-one-related non-tannin tetrahydropyran-2-one, parasorboside. Preliminary biological testing indicates that siliquapyranone exhibits weak activity against both tumour and normal cell lines. This suggests that, like most tannins and parasorboside, siliquapyranone may act as an antifeedant.
Publisher: Wiley
Date: 05-03-2018
Abstract: Counterion-induced stereocontrol is a powerful tool in organic synthesis. However, such enantiocontrol on tetrahedral ammonium cations remains challenging. Described here is the first ex le of using chiral anion phase-transfer catalysis to achieve intermolecular ring-opening of azetidiniums with excellent enantioselectivity (up to 97 % ee). Precise control over the formation and reaction of the chiral ion pair as well as inhibition of the background reaction by the biphasic system is key to the success of the reaction.
Publisher: PeerJ
Date: 04-03-2014
DOI: 10.7717/PEERJ.285
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D1DT04205J
Abstract: This Perspective presents and discusses a selection of rhenium-catalysed carbon–carbon bond-forming reactions and rhenium-catalysed reaction cascades of allyl alcohol substrates.
Publisher: Elsevier BV
Date: 03-2018
Publisher: Elsevier BV
Date: 08-2018
Publisher: Elsevier
Date: 2016
Publisher: CSIRO Publishing
Date: 10-08-2021
DOI: 10.1071/CH21097
Abstract: The alignment of intended learning outcomes for chemistry graduates and the actualised outcomes has been called into question recently. Opportunities to address this lie in the integration of undergraduate learning experiences in which students develop real-world skills and engage with problems that they may encounter as graduates in contemporary workplaces or modern society more broadly. This Highlight article provides an overview of three such approaches, including offering students authentic research experiences within (or outside of) normal degree programs, engaging students in citizen science projects, and considering curriculum reforms to better align with a systems thinking framework. Where possible, we provide explicit ex les grounded in the Australian context, accompanied by some thoughts on the challenges that may be encountered when implementing these approaches in practice.
Publisher: American Chemical Society (ACS)
Date: 29-05-2009
DOI: 10.1021/JO9008386
Abstract: Microwave irradiation of certain chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines in the presence of acetic anhydride and sodium iodide leads, via a trans-halogenation process, to the corresponding iodides in high yield. Related conversions involving pyridines and isoquinolines can also be achieved under similar conditions.
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1OB01946E
Abstract: Gram-scale synthesis of functionalised aryl substituted tetrazinanones for phosgene- and hydrazine-free preparation of 6-oxo-verdazyls.
Publisher: Elsevier
Date: 2021
Publisher: American Chemical Society (ACS)
Date: 18-12-2020
Abstract: This study assesses whether the distinct altitudinal cline in leaf morphology (decreased leaf width and length with increased altitude) in Tasmanian mountain pepper (
Publisher: CSIRO Publishing
Date: 26-07-2022
DOI: 10.1071/CH22108
Abstract: Natural products isolation studies of 16 native Australian fern species have been undertaken, facilitated by pressurised hot water extraction (PHWE). Fourteen of these fern species have not been the subject of natural products isolation research previously. In total, 14 different compounds were isolated from 12 of these 16 different fern species. This included γ- and δ-lactones flavonoid glycosides, a dihydrobenzofuran neolignan, in addition to hydroxycinnamate/caffeic acid esters. More specifically, the lactones 5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-one, 5-(1-hydroxyethyl)-2(5H)-furanone and osmundalin were obtained from Todea barbara, while a dihydrobenzofuran neolignan, (−)-trans-blechnic acid were found in Austroblechnum penna-marina subsp. alpina, and the shikimate ester 5-O-caffeoylshikimic acid was isolated from Parablechnum wattsii. In addition, flavonoids and their glycoside derivatives, kaempferol 3-O-glucopyranoside, 4β-carboxymethyl-(−)-epicatechin, (2R)-eriodictyol-7-O-β-d-glucopyranoside, naringin, quercitrin, quercetin 3-O-(6″-acetyl)-β-d-glucopyranoside, rutin, and tiliroside were isolated from seven other fern species.
Publisher: American Chemical Society (ACS)
Date: 22-10-2009
DOI: 10.1021/JO902032P
Abstract: Operationally simple Au(I)-catalyzed intramolecular hydroarylation (IMHA) reactions of terminal alkynes that proceed in high yield and under very mild conditions are described. These processes involve low catalyst loadings, mild reaction temperatures, and short reaction times, require no cocatalysts or additives, and allow for the generation of a number of important heterocyclic motifs from readily accessible starting materials.
Publisher: Wiley
Date: 13-10-2023
Publisher: Spandidos Publications
Date: 07-02-2020
Publisher: MDPI AG
Date: 18-10-2022
DOI: 10.3390/ENDOCRINES3040055
Abstract: Obesity produces a systemic low-grade inflammation associated with many adverse health conditions and, as we recently learned, with complications of COVID-19. Functional studies in animal models have demonstrated that asperuloside, an iridoid glycoside found in many medicinal plants, has produced promising anti-obesity results. However, the safety profile and the anti-inflammatory properties of asperuloside remain unknown. Here, we confirmed the previously reported anti-obesity properties of asperuloside, and, importantly, we performed toxicity studies assessing cell viability providing a dose reference for future animal experiments. Asperuloside significantly reduced blood levels of leptin and the mRNA levels of orexigenic peptides, such as NPY and AgRP in mice consuming HFD, with no effect on mice eating a standard chow diet. In addition, our results indicate that ASP reduced both hypothalamic and hepatic mRNA levels of pro-inflammatory cytokines such as IL-1, IL-6 and TNF-α as well as the blood levels of plasminogen activator inhibitor-1 (PAI-1), which are known to play a major role in the development of insulin resistance and cardiovascular complications. Collectively, our findings suggest that asperuloside is a safe compound for long-term use in animal models and that it reduces the elevated levels of pro-inflammatory cytokines occurring in obesity.
Publisher: Wiley
Date: 16-06-2023
Abstract: The investigation of distinctive dipole‐transmissive dipolar cycloaddition (DTDC) methodology and the formalisation of this concept is reported. A DTDC procedure was able to be developed by taking advantage of the structural complementarity of azide and diazoalkane 1,3‐dipoles. Intramolecular azide‐alkene 1,3‐DCs followed by spontaneous dipole transmission upon work‐up furnished intermediate α‐diazoisoindole and α‐diazoisoquinoline substrates bearing the key secondary diazoalkane 1,3‐dipole. N ‐Derivatisation of the intermediate α‐diazoisoindole and α‐diazoisoquinolines with a tethered secondary dipolarophile followed by a subsequent 1,3‐DC allowed for rapid construction of a range of functionalised polycyclic N‐heterocycles. Integrated experimental and theoretical studies established requirements for product formation and revealed the likely mechanistic basis of ergent reactivity observed.
Publisher: Wiley
Date: 05-03-2010
Publisher: American Chemical Society (ACS)
Date: 23-12-2022
DOI: 10.1021/ACS.INORGCHEM.1C03336
Abstract: A range of palladium complexes featuring electronically modified, imidazole-based abnormal N-heterocyclic carbene (aNHC) ligands have been prepared in the hopes of accessing a new class of cationic aNHC ligands electronically distinct from normal NHCs and aNHCs. These palladium complexes represent the first ex les of transition metal-ligated aNHC complexes featuring a cationic moiety adjacent to the abnormal carbene center. It was anticipated that these design principles could facilitate electron transfer between the imidazolinylidene and the cationic heterocycle, thus reducing the electron density at the abnormal carbene center. However, this case study suggests that greater conformational restrictions that allow for heterocycle coplanarity are necessary to achieve significant electron transfer and enable access to a new class of cationic charge-appended aNHCs with unique electronic properties.
Publisher: CSIRO Publishing
Date: 2018
DOI: 10.1071/CH18046
Publisher: American Chemical Society (ACS)
Date: 22-08-2013
DOI: 10.1021/JA4060806
Abstract: The use of light to facilitate copper-catalyzed cross-couplings of nitrogen nucleophiles can enable C-N bond formation to occur under unusually mild conditions. In this study, we substantially expand the scope of such processes, establishing that this approach is not limited to reactions of carbazoles with iodobenzene and alkyl halides. Specifically, we demonstrate for the first time that other nitrogen nucleophiles (e.g., common pharmacophores such as indoles, benzimidazoles, and imidazoles) as well as other electrophiles (e.g., hindered/deactivated/heterocyclic aryl iodides, an aryl bromide, an activated aryl chloride, alkenyl halides, and an alkynyl bromide) serve as suitable partners. Photoinduced C-N bond formation can be achieved at room temperature using a common procedure with an inexpensive catalyst (CuI) that does not require a ligand coadditive and is tolerant of moisture and a variety of functional groups.
Publisher: MyJove Corporation
Date: 07-11-2018
DOI: 10.3791/58195
Abstract: A recently developed pressurized hot water extraction (PHWE) method which utilizes an unmodified household espresso machine to facilitate natural products research has also found applications as an effective teaching tool. Specifically, this technique has been used to introduce second- and third-year undergraduates to aspects of natural products chemistry in the laboratory. In this report, two experiments are presented: the PHWE of eugenol and acetyleugenol from cloves and the PHWE of seselin and (+)-epoxysuberosin from the endemic Australian plant species Correa reflexa. By employing PHWE in these experiments, the crude clove extract, enriched in eugenol and acetyleugenol, was obtained in 4-9% w/w from cloves by second-year undergraduates and seselin and (+)-epoxysuberosin were isolated in yields of up to 1.1% w/w and 0.9% w/w from C. reflexa by third-year students. The former exercise was developed as a replacement for the traditional steam distillation experiment providing an introduction to extraction and separation techniques, while the latter activity featured guided-inquiry teaching methods in an effort to simulate natural products bioprospecting. This primarily derives from the rapid nature of this PHWE technique relative to traditional extraction methods that are often incompatible with the time constraints associated with undergraduate laboratory experiments. This rapid and practical PHWE method can be used to efficiently isolate various classes of organic molecules from a range of plant species. The complementary nature of this technique relative to more traditional methods has also been demonstrated previously.
Publisher: Wiley
Date: 08-04-2013
Publisher: American Chemical Society (ACS)
Date: 16-07-2021
DOI: 10.26434/CHEMRXIV-2021-1590N
Abstract: Hypervalent iodine(V) (HVI) compounds are highly efficient reagents for the double oxidative dearomatization of electron-rich phenols to o-quinones. We recently reported that an underexplored class of iodine(V) reagents possessing bidentate bipyridine ligands, termed Bi(N)-HVIs, could efficiently dearomatize electron-poor phenols for the first time. To better understand the fundamental mechanistic basis of this unique reactivity, density functional theory (DFT) was utilized. In this way, different pathways were explored to determine why Bi(N)-HVIs are capable of facilitating these challenging transformations while more traditional hypervalent species, such as IBX cannot. Our calculations reveal that the first redox process is the rate-determining step, the barrier of which hinges on the identity of the ligands bound to the iodine(V) center. This crucial process is composed of three steps: (a) ligand exchange, (b) hypervalent twist, and (c) reductive elimination. We found that strong coordinating ligands disfavour these elementary steps and, for this reason, HVIs bearing such ligands cannot oxidize the electron-poor phenols. In contrast, the weakly coordinating triflate ligands in Bi(N)-HVIs allow for the kinetically favorable oxidation of such phenols {e.g., G‡ = ~22 kcal/mol where Bi(N) = Bi(4-CO2Etbipy)}. It was also identified that trapping triflic acid, which is generated in situ, is a key role played by the basic bidentate bipyridine ligands in Bi(N)-HVIs as this serves to minimize decomposition of the sensitive ortho-quinone product.
Publisher: Wiley
Date: 07-02-2014
Publisher: Elsevier BV
Date: 09-2009
Publisher: CSIRO Publishing
Date: 2018
DOI: 10.1071/CH18283
Abstract: Tasmania is the south-eastern island state of Australia. It is geographically isolated and is recognised for both its rich ersity of plant species and high degree of endemism. Although 530 endemic Tasmanian vascular plant species are known, natural products have only been isolated from 27 of these species (~5.1 %), representing 3 classes (Dicotyledonae, Monocotyledonae, and Gymnospermae), 12 families, and 14 genera. Terpenoids, flavonoids, and alkaloids are the major classes of compound that have been isolated from these species. This report provides the first review of the natural products isolated from endemic Tasmanian plant species and covers ~70 years of research in this area.
Publisher: American Chemical Society (ACS)
Date: 27-04-2021
Publisher: CSIRO Publishing
Date: 2015
DOI: 10.1071/CH15397
Abstract: (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. The use of an alcohol and an ester as the amine precursors was crucial for isolating the cross-metathesis product from the self-metathesis products. This method was also used to prepare two novel analogues of harmonine.
Publisher: Informa UK Limited
Date: 12-2008
Publisher: Wiley
Date: 26-02-2013
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C7RP00249A
Abstract: In chemistry curricula, both the role of the laboratory program and the method of assessment used are subject to scrutiny and debate. The ability to identify clearly defined competencies for the chemistry laboratory program is crucial, given the numerous other disciplines that rely on foundation-level chemistry knowledge and practical skills. In this report, we describe the design, implementation, results, and feedback obtained on a competency-based assessment model recently introduced into the first-year laboratory program at an Australian university. Previously, this laboratory program was assessed via a quantitative, criterion-referenced assessment model. At the core of this new model was a set of competency criteria relating to skills-acquisition, chemical knowledge and application of principles, safety in the laboratory, as well as professionalism and teamwork. By design, these criteria were aligned with the learning outcomes of the course and the degree itself, as well as local accrediting bodies. Qualitative and quantitative feedback from students (and staff) obtained before and after the implementation of this new model suggested this approach provided an enhanced learning experience enabling a greater focus on the acquisition of fundamental laboratory skills and techniques.
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C8MD00582F
Abstract: Naphthoquinones have been investigated as potential therapeutic molecules for neurodegenerative disorders, which is largely based on their anti-oxidative potential.
Publisher: Wiley
Date: 26-03-2009
Publisher: Elsevier BV
Date: 09-2018
Publisher: Wiley
Date: 05-09-2013
Publisher: American Chemical Society (ACS)
Date: 08-12-2016
DOI: 10.1021/ACS.JNATPROD.6B00858
Abstract: Seven new and two known ent-labdane diterpenoids have been isolated from a single plant specimen of Dodonaea viscosa ssp. spatulata, found in Tasmania, Australia. Prior to this study, only seven different labdane diterpenoids had been isolated from D. viscosa. The structures of the natural products were assigned via 1D and 2D NMR spectroscopy and other standard spectroscopic methods. The absolute configuration of three ent-labdane diterpenoids was determined by single-crystal X-ray crystallography of synthetic derivatives. Significantly, the results of this study suggest that the absolute configuration of some known labdane diterpenoids may have been misassigned.
Publisher: Wiley
Date: 23-03-2023
Abstract: Natural products isolation studies were performed on Dodonaea viscosa plant in iduals s led across seven different populations, which revealed considerable intraspecific variation in the terpene profiles across D. viscosa . In total, 14 ent‐ labdane diterpenoids (seven of which are previously unreported), four ent‐ kauranes (one which is previously unreported), one rare norhopene, and two previously unreported monoterpenoid wax esters were isolated. Exceedingly few terpene wax esters have been reported in Nature and the isolation of these unusual secondary metabolites is particularly notable for this reason. In each case, the proposed structures were elucidated employing various standard one‐ and two‐dimensional NMR ( 1 H, 13 C, NOESY, COSY, HSQC, HMBC) spectroscopic techniques and complemented by IR spectroscopy, mass spectrometry, and polarimetry, where appropriate. Synthetic derivatization and X‐ray crystallographic analysis were also employed to further support or secure structural assignments.
Publisher: American Chemical Society (ACS)
Date: 21-01-2014
DOI: 10.1021/JA4126609
Abstract: The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for SN2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as well as a lactam and a 2-oxazolidinone) couple with unactivated secondary (and hindered primary) alkyl bromides and iodides using a single set of comparatively simple and mild conditions: inexpensive CuI as the catalyst, no separate added ligand, and C-N bond formation at room temperature. The method is compatible with a variety of functional groups, such as an olefin, a carbamate, a thiophene, and a pyridine, and it has been applied to the synthesis of an opioid receptor antagonist. A range of mechanistic observations, including reactivity and stereochemical studies, are consistent with a coupling pathway that includes photoexcitation of a copper-amidate complex, followed by electron transfer to form an alkyl radical.
Publisher: Wiley
Date: 08-09-2011
Publisher: Elsevier BV
Date: 04-2018
DOI: 10.1016/J.FITOTE.2017.10.008
Abstract: Pressurised hot water extraction (PHWE) was employed to effect the extraction of two carboxylic acid-containing ent-labdane diterpenoids from Dodonaea viscosa. The different extraction profile provided by PHWE in this case suggests that this recently developed method also has applications as a complementary tool for natural products extraction.
Publisher: Wiley
Date: 03-2016
Publisher: Wiley
Date: 24-04-2008
Publisher: American Chemical Society (ACS)
Date: 26-09-2022
Abstract: The 2-iodoxybenzoic acid (IBX)-controlled oxidative dearomatization of pyrroles occurs very slowly (or not all) in many organic solvents, including DMSO in which IBX is soluble. Interestingly, although IBX is only partially soluble in acetic acid, this solvent mediates the pyrrole oxidative dearomatization. With the aid of density functional theory (DFT) calculations, we have discovered a new mode of reactivity, termed the periodinane oxy-assisted (POA) oxidation mechanism, which explains this observation.
Publisher: Elsevier BV
Date: 09-2018
DOI: 10.1016/J.PHYTOCHEM.2018.05.019
Abstract: An investigation of the previously unexamined ancient Tasmanian clone Lomatia tasmanica W. M. Curtis (Proteaceae) and two other endemic species Lomatia tinctoria R. Br. and Lomatia polymorpha (Labill.) R. Br. was undertaken. This represents the first extensive natural products study in which in idual phytochemical components have been isolated and identified from these three Lomatia species. Extraction of L. tasmanica leaves provided the naphthoquinone juglone (0.34% w/w), and n-alkanes nonacosane and heptacosane (0.30% w/w combined). L. polymorpha afforded the flavonoid glycosides dihydroquercetin 3-O-β-D-xyloside (0.22% w/w) and quercetin 3-O-β-d-glucose (0.14% w/w), as well as the naphthalene glucoside 1,4,8-trihydroxynaphthalene-1-O-β-d-glucose (0.04% w/w) and 4-O-p-coumaroyl-d-glucose (0.03% w/w). In addition, both L. polymorpha and L. tinctoria contained juglone (0.32% w/w and 0.58% w/w, respectively). L. polymorpha provided tetracosan-1-ol, hexacosan-1-ol and octacosan-1-ol (0.07% w/w combined), while L. tinctoria gave nonacosane (0.13% w/w). Analysis of three in idual specimens from each of the three species demonstrated consistency in the respective phytochemical profiles of these populations and tentatively suggests limited intraspecific variation.
Publisher: Elsevier
Date: 2014
Publisher: American Chemical Society (ACS)
Date: 28-07-2022
DOI: 10.1021/ACS.ORGLETT.2C02254
Abstract: The natural product parvistemoamide was isolated in 1991 and has ostensibly eluded synthesis. Its distinctive assigned structure represents the first and only
Publisher: American Chemical Society (ACS)
Date: 20-08-2012
DOI: 10.1021/JA306323X
Publisher: Wiley
Date: 03-12-2022
Abstract: Polycyclic alkaloid natural products featuring pyrrolidine and pyrrolidinone motifs remain enduring targets of total synthesis endeavors. Pyrrole and its derivatives have been exploited to access many such frameworks, including alkaloids belonging to the Aspidosperma , Stemona , and batzelladine families. In this article, a selection of exemplars that highlight the utility of pyrrole‐based approaches to facilitate total syntheses of pyrrolidine‐ and pyrrolidinone‐containing alkaloids and related molecules are showcased.
Publisher: American Chemical Society (ACS)
Date: 13-04-2021
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8CC02244E
Abstract: The results of a proof-of-concept study demonstrate for the first time that pulsed LED irradiation enhances the rate of product formation and the yield of a visible light-mediated photoredox-catalysed reaction.
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5OB01573A
Abstract: Polygodial, was efficiently extracted and isolated in gram-scale quantities (3.3% w/w) from Tasmannia lanceolata (Tasmanian native pepper) using a pressurised hot water extraction (PHWE) technique that utilises an unmodified household espresso machine.
Publisher: Wiley
Date: 06-11-2009
Publisher: MDPI AG
Date: 04-12-2018
DOI: 10.3390/CATAL8120620
Abstract: Ongoing research exploring the chemistry of N-heterocyclic carbenes (NHCs) has led to the development and discovery of new NHC subclasses that deviate beyond Arduengo’s prototypical N,N′-disubstituted imidazol-2-ylidene-based structures. These systems continue to enable and extend the fundamental role of NHC ligands in synthesis and catalysis. In this regard, the advent of protic NHCs has garnered particular interest. This derives in part from their applications to the selective preparation of unique molecular scaffolds and their unprecedented bifunctional reactivity, which can be exploited in transition metal-catalyzed processes. In comparison, the synthetic applications of closely related anionic naked NHCs remain rather underexplored. With this in mind, this review highlights the interesting fundamental properties of non-classical anionic naked NHCs, and focuses on their emerging applications in synthesis and catalysis.
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D0PY01159B
Abstract: We report the preparation of thermoresponsive hydrogels via free-radical polymerization and crosslinking of NIPAM based deep eutectic monomer solvents (DEMs).
Publisher: ARKAT USA, Inc.
Date: 04-09-2022
Publisher: Elsevier
Date: 2021
Publisher: Wiley
Date: 26-05-2021
Abstract: Palladium(II) boronates are recognized as fundamental pre‐transmetalation intermediates in Suzuki–Miyaura cross‐couplings. While these typically transient species have been detected and studied spectroscopically, it is conspicuous that they have never been isolated since this important reaction was discovered over forty years ago. This study reports the synthesis of a family of unprecedented arylpalladium(II) boronates that are, by design, kinetically stable at ambient temperature, both in solution and in the solid state. These properties enabled unambiguous crystallographic confirmation of their structure for the first time and their chemical competence in a Suzuki–Miyaura reaction was demonstrated.
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6NP00070C
Abstract: The total synthesis of natural products and their derivatives continues to inspire organic chemists to identify and test new synthetic strategies and develop and explore novel methodology.
Publisher: American Chemical Society (ACS)
Date: 19-08-2021
Publisher: Elsevier
Date: 2018
Publisher: Wiley
Date: 13-03-2017
Publisher: MDPI AG
Date: 19-10-2021
Abstract: In a search of small molecules active against apoptosis-resistant cancer cells, including glioma, melanoma, and non-small cell lung cancer, we previously prepared α,β- and γ,δ-unsaturated ester analogues of polygodial and ophiobolin A, compounds capable of pyrrolylation of primary amines and demonstrating double-digit micromolar antiproliferative potencies in cancer cells. In the current work, we synthesized dimeric and trimeric variants of such compounds in an effort to discover compounds that could crosslink biological primary amine containing targets. We showed that such compounds retain the pyrrolylation ability and possess enhanced single-digit micromolar potencies toward apoptosis-resistant cancer cells. Target identification studies of these interesting compounds are underway.
Publisher: Elsevier
Date: 2020
Publisher: American Chemical Society (ACS)
Date: 14-09-2018
Publisher: Elsevier BV
Date: 04-2020
Publisher: Wiley
Date: 02-07-2020
Publisher: Frontiers Media SA
Date: 13-04-2021
DOI: 10.3389/FENDO.2021.615446
Abstract: Asperuloside is an iridoid glycoside found in many medicinal plants that has produced promising anti-obesity results in animal models. In previous studies, three months of asperuloside administration reduced food intake, body weight, and adipose masses in rats consuming a high fat diet (HFD). However, the mechanisms by which asperuloside exerts its anti-obesity properties were not clarified. Here, we investigated homeostatic and nutrient-sensing mechanisms regulating food intake in mice consuming HFD. We confirmed the anti-obesity properties of asperuloside and, importantly, we identified some mechanisms that could be responsible for its therapeutic effect. Asperuloside reduced body weight and food intake in mice consuming HFD by 10.5 and 12.8% respectively, with no effect on mice eating a standard chow diet. Fasting glucose and plasma insulin were also significantly reduced. Mechanistically, asperuloside significantly reduced hypothalamic mRNA ghrelin, leptin, and pro-opiomelanocortin in mice consuming HFD. The expression of fat lingual receptors (CD36, FFAR1-4), CB1R and sweet lingual receptors (TAS1R2-3) was increased almost 2-fold by the administration of asperuloside. Our findings suggest that asperuloside might exert its therapeutic effects by altering nutrient-sensing receptors in the oral cavity as well as hypothalamic receptors involved in food intake when mice are exposed to obesogenic diets. This signaling pathway is known to influence the subtle hypothalamic equilibrium between energy homeostasis and reward-induced overeating responses. The present pre-clinical study demonstrated that targeting the gustatory system through asperuloside administration could represent a promising and effective new anti-obesity strategy.
Publisher: Wiley
Date: 05-03-2018
Publisher: Wiley
Date: 07-2023
Abstract: Natural products isolation studies were performed on two Dodonaea species. This led to the discovery of one previously unreported prenylated flavonoid bearing a malonic acid moiety and six known compounds from the aerial parts of Dodonaea filiformis . In addition, three previously unreported natural products (another malonic‐acid‐containing prenylated flavonoid, a prenylated flavonoid and an ent ‐labdane diterpenoid) and seven known compounds were found from the flowers of D. viscosa . Furthermore, as a result of this work, a revised structure is proposed for a prenylated flavonoid previously isolated from D. viscosa .
Publisher: Informa UK Limited
Date: 28-04-2021
Publisher: Wiley
Date: 04-2015
DOI: 10.1890/ES14-00198.1
Publisher: CSIRO Publishing
Date: 17-05-2022
DOI: 10.1071/CH21334
Abstract: The teaching laboratory remains an important environment for developing undergraduate chemists, but the inherent ersity of inorganic chemistry results in less standardised undergraduate curricula than other sub-disciplines. This study surveys the content of advanced (third-year) inorganic chemistry across Australia and reviews experimental materials from 15 universities that offer inorganic laboratory programmes at this level. All institutions offer at least one traditional inorganic experiment, the most common being the preparation and acetylation of ferrocene, spectroscopy and magnetochemistry of nickel coordination compounds and palladium-catalysed cross-couplings. These inorganic classics are complemented by a breadth of non-traditional offerings that often align with institutional research strengths. Academic unit coordinators were also surveyed and their responses interpreted using ASELL (Advancing Science and Engineering through Laboratory Learning) tools. Advanced inorganic laboratory programmes were found to develop students’ practical and transferrable skills. Students generally receive guidance from teaching staff in all aspects of experimental work, including planning, development, analysis and communicating conclusions. Academic unit coordinators identified potential improvements that included ersifying student activities in the lab and how they are being assessed.
Publisher: Wiley
Date: 05-04-2013
Publisher: Springer Science and Business Media LLC
Date: 24-04-2019
Publisher: Wiley
Date: 26-05-2021
Abstract: Palladium(II) boronates are recognized as fundamental pre‐transmetalation intermediates in Suzuki–Miyaura cross‐couplings. While these typically transient species have been detected and studied spectroscopically, it is conspicuous that they have never been isolated since this important reaction was discovered over forty years ago. This study reports the synthesis of a family of unprecedented arylpalladium(II) boronates that are, by design, kinetically stable at ambient temperature, both in solution and in the solid state. These properties enabled unambiguous crystallographic confirmation of their structure for the first time and their chemical competence in a Suzuki–Miyaura reaction was demonstrated.
Publisher: Elsevier BV
Date: 2022
DOI: 10.1016/J.FITOTE.2021.105088
Abstract: The first natural product isolation studies of Nothofagus gunnii (Hook.f.) Oerst and Nothofagus cunninghamii (Hook.f.) Oerst have been undertaken. A previously unreported stilbene derivative, pinosylvin monoacetate, was isolated from the leaves of N. gunnii, in addition to 14 known compounds including the flavonoids galangin, pinobanksin, catechin and quercetin sesquiterpenoids such as, ilicol and (+)-β-costol acetate 2,4-dihydroxy-6-methoxychalcone and pinosylvin. Four known flavonoid natural products, catechin, quercetin, ayanin, and avicularin were isolated from the leaves of N. cunninghamii. This study reveals that N. gunnii is a rich source of flavonoid, chalcone and stilbene compounds, while primarily hydroxyflavonoid compounds are found in N. cunninghamii. The isolated phytochemicals are consistent with the evolutionary relationships suggested to exist among Nothofagus species.
Publisher: American Chemical Society (ACS)
Date: 19-06-2019
Publisher: Wiley
Date: 03-2016
Publisher: American Chemical Society (ACS)
Date: 13-01-2022
DOI: 10.1021/ACS.INORGCHEM.1C02964
Abstract: This report details the synthesis and characterization of a small family of previously unreported, structurally related chromium, molybdenum, tungsten, manganese, and iron complexes bearing N-heterocyclic carbene and carbonyl supporting ligands. These complexes have the general form [ML(CO)
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C7OB03144K
Abstract: In this report, we review the methods that have been employed to synthesise annulated pyrroles.
Publisher: Georg Thieme Verlag KG
Date: 16-02-2009
Publisher: American Chemical Society (ACS)
Date: 28-02-2019
Publisher: Wiley
Date: 16-08-2018
Abstract: Platelet-activating factor (PAF) and its receptor (PAFr) have been implicated in a wide range of diseases and disorders that originate from the activation of inflammatory pathways. Although the exact structure of the binding site on the PAFr remains unknown, the PAFr is a well-established therapeutic target, and an array of structurally erse PAFr antagonists have been identified. These include compounds that are structurally similar to the natural PAF ligand, synthetic heterocycles, complex polycyclic natural products, and various metal complexes. This review provides an update on more than 20 years of progress in this area. The development and synthesis of new PAFr antagonists, structure-activity relationship studies, the biological activity of these molecules, and their therapeutic potential are discussed.
Publisher: American Chemical Society (ACS)
Date: 06-2023
Publisher: Informa UK Limited
Date: 08-07-2022
Publisher: Elsevier
Date: 2015
Publisher: Elsevier
Date: 2023
Publisher: CSIRO Publishing
Date: 2011
DOI: 10.1071/CH10465
Abstract: N-Arylazetidin-2-ones of the general form 1, which are readily prepared by Goldberg–Buchwald-type copper-catalyzed coupling of N-unsubstituted azetidin-2-ones with the relevant aryl halide or using Mitsunobu cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 0–18°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0 M aqueous sodium hydroxide ropan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).
Publisher: Wiley
Date: 07-08-2014
Publisher: Elsevier BV
Date: 08-2019
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3CC00882G
Abstract: This Highlight examines key strategies that have enabled the structural authentication of important species that shed light on fundamental on-cycle intermediates in transition-metal-catalysed cross-couplings.
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3PY00294B
Abstract: We report the preparation of thermoresponsive block copolymers via the simultaneous RAFT polymerization and anionic ring-opening polymerization (ROP) of N- isopropylacylamide and ε-caprolactone respectively, in the absence of traditional solvents.
Publisher: Georg Thieme Verlag KG
Date: 18-11-2022
DOI: 10.1055/A-1982-5433
Abstract: Substituted morpholine derivatives appear frequently in biologically active compounds and thus novel routes towards such structures are of great synthetic interest. Herein, we report the total syntheses of chelonin A, a morpholine-derived marine natural product with reported antibacterial and anti-inflammatory activity. The key step in this process was a rhodium carbenoid 1,3-insertion into a bromohydrin O–H bond, followed by annulation, leading to a 2,6-disubstituted-3,4-dihydro-2H-1,4-oxazine core. This work was then extended to deliver the first asymmetric total synthesis of (–)-chelonin A using an enantioenriched bromohydrin, prepared in turn via asymmetric transfer hydrogenation of an α-bromoketone.
Publisher: Spandidos Publications
Date: 05-10-2018
Publisher: American Chemical Society (ACS)
Date: 17-12-2018
DOI: 10.26434/CHEMRXIV.7472051.V1
Abstract: The synthesis, characterization, photophysical and photocatalytic studies of anionic platinum(II) tetrazolato complexes, with the general structure [TBA][Pt(CNC)TzR], are reported, where CNC 2- represents a doubly cyclometalated 2,4,6-triphenylpyridine, TzR - is an anionic 5-substituted tetrazolato ligand (with a variable R functional group) and TBA + is the tetrabutylammonium countercation. The complexes were prepared by substitution of the DMSO ligand in [Pt(CNC)(DMSO)] with the corresponding tetrazolato ligand. No emission from the platinum(II) complexes was detected at room temperature in solution, but the photophysical properties could be assessed in the solid state, where all the complexes display emission bands attributed to aggregates. The platinum(II) complexes were found to facilitate a range of fundamental classes of visible-light-mediated photoredox-catalyzed reactions, including α‑amino C–H functionalization processes, such as Povarov-type reactions and the addition of α-amino C–H bonds across Michael acceptors, in addition to ATRA chemistry, and a hydrodeiodination. With the exception of the hydrodeiodination process, the best Pt(II) catalysts provided turnover numbers of 150–175 in each of these transformations.
Publisher: Elsevier BV
Date: 08-2022
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9DT02533B
Abstract: This study demonstrates that structurally- erse, photoactive rhenium( i ) tricarbonyl complexes can mediate representative atom-transfer radical addition, hydrodehalogenation, and α-amino C–H functionalisation reactions.
Publisher: American Chemical Society (ACS)
Date: 14-10-2022
Publisher: American Chemical Society (ACS)
Date: 22-03-2023
Start Date: 03-2021
End Date: 03-2025
Amount: $560,000.00
Funder: Australian Research Council
View Funded ActivityStart Date: 03-2021
End Date: 12-2025
Amount: $914,404.00
Funder: Australian Research Council
View Funded ActivityStart Date: 2023
End Date: 12-2026
Amount: $799,084.00
Funder: Australian Research Council
View Funded Activity