283 results for Brimble, Margaret

  • GPE Analogs and Peptidomimetics

    Abood, NA; Brimble, Margaret (2003-03-20)

    Patent
    The University of Auckland Library

    This invention relates to analogs and peptidomimetics of glycyl-L-prolyl-L-glutamic acid (GPE). In particular, this invention relates to GPE analogs and peptidomimetics that are anti-apoptotic and anti-necrotic, to methods of making them, to pharmaceutical compositions containing them, and to their use.

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  • A synthetic study towards aryl 6,6-spiroacetal analogues of rubromycin

    Choi, Peter; Rathwell, DC; Brimble, Margaret (2008)

    Conference poster
    The University of Auckland Library

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  • Treatment of non-convulsive seizures in brain injury using G-2-methyl-prolyl glutamate

    Gluckman, Peter; Brimble, Margaret; Wilson, D; Tortella, FC; Williams, AJ; Xi-Chun, ML; Hartings, JA; Gryder, D (2010-05-11)

    Patent
    The University of Auckland Library

    Aspects of this invention include the use of G-2MePE to treat patients with brain injury characterized by non-convulsive seizures. G-2MePE is useful in treating brain injuries caused by traumatic brain injury, stroke, hypoxia/ischemia and toxic injury.

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  • Pyrans and their Benzo Derivatives: Synthesis

    Brimble, Margaret; Sperry, Jonathan; Gibson, JS (2008)

    Book item
    The University of Auckland Library

    The abundance of six-membered oxygen containing heterocycles in bioactive natural products continues to encourage the development of new and improved syntheses. There is a vast amount of new literature dedicated to the synthesis of pyrans and their benzo derivatives; however, many traditional approaches are still of great value and this chapter should be read in conjunction with the corresponding chapters in the first and second editions of Comprehensive Heterocyclic Chemistry ....

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  • Di-(-)-(1R,2S)-2-phenyl-1-cyclohexyl Diazenedicarboxylate

    Brimble, Margaret (2002)

    Book item
    The University of Auckland Library

    InChI = 1S/C26H30N2O4/c29-25(31-23-17-9-7-15-21(23)19-11-3-1-4-12-19)27-28-26(30)32-24-18-10-8-16-22(24)20-13-5-2-6-14-20/h1-6,11-14,21-24H,7-10,15-18H2/b28-27+/t21-,22-,23+,24+/m0/s1 InChIKey = RHBWBKFUCXVAMA-KQEKZTIUSA-N (reagent used as a chiral azo-enophile in asymmetric azo-ene reactions) Alternate Name: (1R-{1??[E(1R*,2S*)],2??})-Bis(2-phenylcyclohexyl) diazenedicarboxylate. Physical Data: [??]D ???56.9 (c 0.65, CHCl3). Solubility: soluble in CH2Cl2, diethyl ether, and most organic solvents. Form Supplied in: yellow oil. Analysis of Reagent Purity: 1H NMR, IR, TLC, elemental analysis. Preparative Methods: The title reagent is prepared1 by reaction of (1R, 2S)-2-phenyl-1-cyclohexanol with excess phosgene in the presence of quinoline to afford a chloroformate which is treated directly with hydrazine monohydrate (0.5 equiv) to afford di-(???)-(1R, 2S)-2-phenyl-1-cyclohexyl diazanedicarboxylate. Oxidation of the diazanedicarboxylate to the diazenedicarboxylate is then readily effected using N-bromosuccinimide and pyridine (eq 1).

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  • Synthesis of Benzotriazole Analogues of the Helicobactericidal Agents CJ-13,015, CJ-13,102, CJ-13,108, and CJ-13,104 Using a Regioselective 1,3-Dipolar Cycloaddition

    Atkinson, Darcy; Sperry, Jonathan; Brimble, Margaret (2011)

    Journal article
    The University of Auckland Library

    A regioselective 1,3-dipolar cycloaddition of a disubstitilted aryne and various alkyl azides facilitates access to benzotriazole analogues of several anti-Helicobacter pylori antibiotics.

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  • Equipment Access for Graduate Students - The First Hurdle

    Brimble, Margaret (2007)

    Journal article
    The University of Auckland Library

    Last month, Academy Councillor Carolyn Burns reflected on the unwieldy systems of compliance and accountability that our researchers face. These systems affect our opportunities to conduct cutting edge science in New Zealand, to attract excellent scientists from overseas, and to retain some of our best research scientists here. ...

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  • Professor Jim Coxon. A Tribute

    Brimble, Margaret; Steel, P (2006)

    Journal article
    The University of Auckland Library

    This special issue of the ARKIVOC is dedicated to Professor Jim Coxon to mark his 65 th birthday and acknowledge his contribution to New Zealand science through his diverse achievements in mechanistic organic chemistry carried out at the University of Canterbury.

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  • Synthesis of a Dimeric Pyranonaphthoquinone via a Novel Double Furofuran Annulation Strategy

    Brimble, Margaret; Neville, D; Duncalf, Letecia (1998)

    Journal article
    The University of Auckland Library

    The first synthesis of a dimeric pyranonaphthoquinone 16 which is related to the naturally occurring dimeric pyranonaphthoquinones, e.g. actinorhodin 1 and crisamycin 3, is described. The key biaryl 8 is prepared by means of a Suzuki coupling reaction, utilizing the Miyaura reagent to generate the organoboron coupling partner. The first example of a double annulation of a bisquinone with 2-trimethylsilyloxyfuran to afford a bisfuronaphthofuran and subsequent double oxidative rearrangement to a dimeric pyranonaphthoquinone is described.

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  • Synthesis of a Functionalized Bis-Spiroacetal

    Brimble, Margaret; Williams, GM; Baker, R; James, M (1990)

    Journal article
    The University of Auckland Library

    The synthesis of bis-spiroacetal (15) bearing an hydroxymethyl group at C-2 is described establishing a methodology for preparation of the polyether antibiotics salinomycin and narasin. Formation of an important iodohydrin intermediate has been accomplished by a highly efficient reaction of an epoxide with LiI catalysed by BF3.Et2O in THF. Displacement of the resulting neopentyl iodide was achieved in high yield by reaction of the iodide with potassium superoxide in dimethylsulphoxide/tetrahydrofuran in the presence of 18-crown-6. The synthesis of bis-spiroacetal (15) has been achieved the following sequence.

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  • Synthesis of a New Spiroacetal Based Herbicide

    Brimble, Margaret; Johnston, Andrew; Furneaux, RH (1997)

    Journal article
    The University of Auckland Library

    [3R???, 5S???, 6S???]-3-Benzyloxy-5-methoxy-1,7-dioxaspiro[5.5]undecane 3 and [3R???, 5S???, 6S???]-3-methoxy-5-benzyloxy-1,7-dioxaspiro[5.5]undecane 4 were prepared making use of a base induced rearrangement of a 4,5-epoxy-1,7-dioxaspiro[5.5]undecane.

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  • SYNTHESIS OF A PYRANONAPHTHOQUINONE-SPIROACETAL

    Brimble, Margaret; NAIRN, M (1992-03)

    Journal article
    The University of Auckland Library

    A synthesis of pyranonaphthoquinone-spiroacetal 12 is reported which represents an efficient entry to the pentacyclic framework of the pyranonaphthoquinone antibiotic griseusin A. The key step involves assembly of the furo[3,2-b]naphtho[2,3-d]pyran 11via a ceric ammonium nitrate oxidative rearrangement of the furo[3,2-b]naptho[2,1-d]furan 10. This latter heterocycle 10 in turn was constructed via the uncatalysed 1,4-addition of 2-trimethylsilyloxyfuran 9 to naphthoquinone 8. Naphthoquinone 8 is readily available from 1,4-dimethoxynaphthalene-2-carbaldehyde 3 and acetylene 4.

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  • A Convergent Synthesis of the [4.4]-Spiroacetal-gamma-lactones Cephalosporolides E and F

    Brimble, Margaret; Finch, OC; Heapy, AM; Fraser, JD; Furkert, DP; O'Connor, PD (2011)

    Journal article
    The University of Auckland Library

    A short convergent synthesis of the fungal metabolites cephalosporolides E and F is reported. The key step makes use of a chelation-controlled Mukaiyam

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  • Synthesis of the Bis-Spiroacetal Moiety of 17-epi-20-Deoxysalinomycin

    Brimble, Margaret; Williams, GM (1992)

    Journal article
    The University of Auckland Library

    The synthesis of the bis-spiroacetal moiety of 17-epi-20-deoxysalinomycin (4) is reported in which the key step involves oxidative cyclization of the hydroxy spiroacetals 14 and 15 to the bis-spiroacetals 16 and 17 using (diacetoxyiodo)benzene and iodine under photolytic conditions.

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  • SYNTHESIS OF THE INSECT FEEDING DETERRENT PERAMINE VIA MICHAEL ADDITION OF A PYRROLE ANION TO A NITROALKENE

    Brimble, Margaret; ROWAN, DD (1990-02-01)

    Journal article
    The University of Auckland Library

    A total synthesis of peramine (1), the major insect feeding deterrent isolated from perennial ryegrass (Lolium perenne L.) infected with the endophytic fungus Acremonium lolii is reported. The key step involves the Michael addition of the potassium salt of methyl pyrrole-2-carboxylate (3) to the nitroalkene (4) providing access to a 3-substituted pyrrolo[1,2-a]pyrazin-1 (2H)-one (10). Displacement of the allylic bromide (11) by cyanomethyl cuprate provided the methodology for introducing the desired monosubstituted guanidino group via the nitrite (12).

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  • Gold(I)-catalysed intramolecular hydroamination of ??-quaternary alkynes: synthetic studies towards spiroimine marine toxins

    Zhang, YC; Furkert, Daniel; Gu??ret, SM; Lombard, F; Brimble, Margaret (2011)

    Journal article
    The University of Auckland Library

    Cyclic spiroimines form an essential component of the bioactive pharmacophore in a number of potent fast-acting marine biotoxins, including the pinnatoxins, gymnodimine and the spirolides. These present a significant challenge for the total synthesis of this class of natural products. A novel approach to these cyclic spiroimines based on metal-catalysed hydroamination of spiroaminoalkyne precursors is reported herein. Au(PPh3)SbF6 was found to effect the formation of bench-stable 5,6- and 6,6-spiroimine systems in high yields, although the 7,6-analogue remained elusive. To the best of our knowledge these are the first reported examples of ??-quaternary cyclic imines formed via alkyne hydroamination.

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  • Synthesis of the FG ring fragment of pectenotoxins 1-9

    Heapy, Amanda; Brimble, Margaret (2010)

    Journal article
    The University of Auckland Library

    The synthesis of the FG ring fragment common to pectenotoxins 1-9 is reported. The successful, convergent synthesis relied on high yielding routes to access two key intermediates; aldehyde 1 and phosphonium salt 2. A Z-selective Wittig reaction gave access to advanced linear precursor 3, which was converted to FG ring fragment 4 using two sequential cyclization reactions. (C) 2010 Elsevier Ltd. All rights reserved.

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  • [3R*,5S*,6S*]-1,7-dioxaspiro[5.5]undec-3,5-diyl bis(3,5-dinitrobenzoate)

    Brimble, Margaret; Johnston, AD (1997-01-01)

    Journal article
    The University of Auckland Library

    To a solution of [3R*,5S8,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (50 mg, 0.27 mmol) in dichloromethane (5.0 cm3), was added triethylamine (60 mg, 0.59 mmol), 4-dimethylaminopyridine (~1 mg), 3,5-dinitrobenzoyl chloride (136 mg, 0.59 mmol) and the resultant solution allowed to stand at room temperature for 120 h. Removal of the solvent at reduced pressure gave a pale yellow oil, that was purified by flash chromatography using hexane-ethyl acetate (6:4) as eluent to afford the title compound (1) (61 mg, 39%) as pale yellow plates.

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  • Addition of 2-tert-Butyldimethylsilyloxythiophene to Activated Quinones: An Approach to Thia Analogues of Kalafungin

    Brimble, Margaret; Laita, Olivia; Robinson, James (2006)

    Journal article
    The University of Auckland Library

    The uncatalyzed reaction of 2-tert-butyldimethylsilyloxythiophene 2 with 1,4-quinones bearing either an electron withdrawing acetyl or a carbomethoxy group at C-2, was investigated. No reaction was observed using 1,4-quinones 8 and 9 bearing an ester group at C-2 whereas use of 1,4-quinones 10 and 11 bearing an acetyl group at C-2 only provided low yields of the silyloxythiophenes 15 and 16 resulting from electrophilic substitution of the silyloxythiophene by the 1,4-quinone. Use of the Lewis acids InCl3, Cu(OTf)2 and BF3??Et2O were investigated in an effort to improve the yield of the desired annulation reaction. BF3??Et2O proved to be the optimum catalyst for the synthesis of thiolactone naphthofuran adducts 14 and 18 from 1,4-naphthoquinones 9 and 11, respectively. Reaction of 2-tert-butyldimethylsilyloxythiophene 2 with 1,4-benzoquinones 8 and 10 bearing a carbomethoxy or an acetyl group at C-2, respectively, afforded thiolactone benzofuran adducts 13 and 17, respectively, catalyzed by either InCl3 or Cu(OTf)2. Addition of 2-tert-butyldimethylsilyloxythiophene 2 to 3-acetyl-5-methoxy-1,4-naphthoquinone 12 afforded adduct 19 that underwent oxidative rearrangement to thiolactone pyranonaphthoquinone 20 using ceric ammonium nitrate in acetonitrile, thus providing a novel approach for the synthesis of a thia analogue of the pyranonaphthoquinone antibiotic kalafungin.

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  • Synthesis of 6,6-Bisbenzannulated Spiroketals Related to the Rubromycins Using a Double Intramolecular Hetero-Michael Addition (DIHMA)

    Choi, Peter; Rathwell, Dominea; Brimble, Margaret (2009)

    Journal article
    The University of Auckland Library

    The synthesis of a series of 6,6-bisbenzannulated spiroketals using a novel microwave-assisted DIHMA approach is reported. Coupling of an aryl acetylene and an aryl aldehyde via acetylide anion addition resulted in the formation of an alkynol which was followed by oxidation to the desired ynone. Spirocyclization using the DIHMA protocol afforded the desired bisbenzannulated spiroketal in good yield.

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