Browsing Chemistry Faculty Research, Publications and Presentations by Author "Thompson, Alison"

Now showing items 1-20 of 22

  • Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and Alkenes 

    Published version: Figliola, C., Robertson, K., Greening, S., & Thompson, A. (2017). Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and Alkenes. Journal of Organic Chemistry (June 24, 2017)

  • Asymmetric oxidation of 2-(arylsulfenyl)pyrroles 

    Thompson, Alison, Jose R. Garabatos-Perera, and H. Martin Gillis. 2008. "Asymmetric oxidation of 2-(arylsulfenyl)pyrroles." Canadian Journal of Chemistry-Revue Canadienne De Chimie 86(7): 676-681.
    The asymmetric oxidation of prochiral 2-(arylsulfenyl)pyrroles has been investigated. A marked electronic effect within the substrate significantly influenced the degree of enantioselectivity obtained, with very high enantio ...

  • Chiral molecules containing the pyrrole framework 

    Thirumalairajan, Srinath, Beth M. Pearce, and Alison Thompson. 2010. "Chiral molecules containing the pyrrole framework." Chemical Communications 46(11): 1797-1812.
    This review summarizes strategies by which chiral pyrroles, both simple and complex, have been prepared: strategies include formation of the pyrrolic ring using starting materials appended with chirality, as well as the ...

  • Chloride anion transport and copper-mediated DNA cleavage by C-ring functionalized prodigiosenes 

    Diaz, Rosa I. Saez, Jasmine Regourd, Paul V. Santacroce, Jeffery T. Davis, et al. 2007. "Chloride anion transport and copper-mediated DNA cleavage by C-ring functionalized prodigiosenes." Chemical Communications: 2701-2703.
    A new class of prodigiosenes with stability-enhancing functionalities appended to the C-ring were found to transport chloride anions through liposomal membranes, as well as to induce copper-mediated DNA cleavage.

  • Cl-BODIPYs: a BODIPY class enabling facile beta-substitution 

    Lundrigan, Travis, Sarah M. Crawford, T. Stanley Cameron, and Alison Thompson. 2012. "Cl-BODIPYs: a BODIPY class enabling facile beta-substitution." Chemical Communications 48(7): 1003-1005.
    Cl-BODIPYs, synthesized in high yields from dipyrrins under air- and moisture-free conditions, are extremely facile to substitution at boron compared to their corresponding F-BODIPYs, opening up a new route to BODIPYs ...

  • Conversion of F-BODIPYs to Cl-BODIPYs: Enhancing the Reactivity of F-BODIPYs 

    Lundrigan, Travis, and Alison Thompson. 2013. "Conversion of F-BODIPYs to Cl-BODIPYs: Enhancing the Reactivity of F-BODIPYs." Journal of Organic Chemistry 78(2): 757-761.
    A new method for the synthesis of Cl-BODIPYs from F-BODIPYs is reported, merely requiring treatment of the F-BODIPY with boron trichloride. Cl-BODIPYs are exploited as synthetic intermediates generated in situ for the ...

  • Eight-Membered Ring-Containing Jadomycins: Implications for Non-enzymatic Natural Products Biosynthesis 

    Published version: Robertson AW, Martinez-Farina CF, Smithen DA, Yin H, Monro S, Thompson A, McFarland SA, Syvitski RT, Jakeman DJ. (2015). Eight-Membered Ring-Containing Jadomycins: Implications for Non-enzymatic Natural Products Biosynthesis. Journal of the American Chemical Society, 137, 3271-3275. doi: 10.1021/ja5114672

  • The first series of alkali dipyrrinato complexes 

    Ali, Adeeb Al-Sheikh, Judy Cipot-Wechsler, Sarah M. Crawford, Omar Selim, et al. 2010. "The first series of alkali dipyrrinato complexes." Canadian Journal of Chemistry-Revue Canadienne De Chimie 88(8): 725-735.
    The first series of alkali dipyrrinato complexes is reported, encompassing lithium, sodium, and potassium salts of meso-unsubstituted and meso-aryl-substituted derivatives. By varying the substituents at the meso position, ...

  • Investigations into the nucleophilic meso-substitution of F-BODIPYs and improvements to the synthesis of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene. 

    Crawford, Sarah M., and Alison Thompson. 2011. "Investigations into the nucleophilic meso-substitution of F-BODIPYs and improvements to the synthesis of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene." Heterocycles 83(2): 311-322.
    A series of three F-BODIPYs, with varying levels of steric crowding about the meso-position were selected to investigate nucleophilic meso-substitution of F-BODIPYs. The synthesis of one of these F-BODIPYs, 4,4-difluor ...

  • Investigations regarding the utility of prodigiosenes to treat leukemia 

    Smithen, Deborah A., A. Michael Forrester, Dale P. Corkery, Graham Dellaire, et al. 2013. "Investigations regarding the utility of prodigiosenes to treat leukemia." Organic & Biomolecular Chemistry 11(1): 62-68.
    Prodigiosenes, possessing a 4-methoxypyrrolyldipyrrin skeleton, are known for their anti-cancer activity. Structural modification of the C-ring resulted in a series of prodigiosenes that displayed promising activity against ...

  • Microwave-accelerated synthesis of benzyl 3,5-dimethyl-pyrrole-2-carboxylate 

    Regourd, Jasmine, Ian M. Comeau, Cory S. Beshara, and Alison Thompson. 2006. "Microwave-accelerated synthesis of benzyl 3,5-dimethyl-pyrrole-2-carboxylate." Journal of Heterocyclic Chemistry 43(6): 1709-1714.
    Benzyl 3,5-dimethyl-pyrrole-2-carboxylate, a very useful pyrrole in porphyrin and dipyrromethene synthesis, can be synthesized via the Knorr-type reaction, but in low yield. Alternative routes to benzyl 3,5-dimethyl-pyrr ...

  • Probing the Hydrolytic Reactivity of 2-Difluoromethyl Pyrroles 

    Published version: Melanson JA, Figliola C, Smithen DA, Kajetanowicz AK, Thompson A. (2017). Probing the Hydrolytic Reactivity of 2-Difluoromethyl Pyrroles. Organic and Biomolecular Chemistry. 15, 144-152. doi:10.1039/c6ob01441k

  • Prodigiosenes Conjugated to Tamoxifen and Estradiol 

    Published version: Marchal E1, Figliola C, Thompson A. (2017) Prodigiosenes Conjugated to Tamoxifen and Estradiol. Organic and Biomolecular Chemistry, 15(25):5410-5427. doi: 10.1039/c7ob00943g

  • Robust Synthesis of F-BODIPYs 

    Publisher's version: Beh, Michael; Douglas, Katherine; House, Kelsey; Murphy, Alexandra; Sinclair, Jackson; and Thompson, Alison. Robust Synthesis of F-BODIPYs. Org. Biomol. Chem. 2016, 14, 11473-11479. DOI: 10.1039/c6ob02238c
    F-BODIPYs are widely used in applications that rely upon their highly tunable optical properties. A protocol is established for the high-yielding synthesis of F-BODIPYs involving non-anhydrous reagents and not requiring ...

  • Synthesis and Anticancer Activity of Prodigiosenes bearing C-Ring Esters and Amides 

    Published version: Lund, K., Figliola, C., Kajetanowicz, A. & Thompson, A. (2017) Synthesis and Anticancer Activity of Prodigiosenes bearing C-Ring Esters and Amides, RSC Advances, 50 (7), 18617. doi: 10.1039/c7ra01628j

  • Synthesis and characterisation of the unsubstituted dipyrrin and 4,4-dichloro-4-bora-3a,4a-diaza-s-indacene: improved synthesis and functionalisation of the simplest BODIPY framework 

    Groves, Brandon R., Sarah M. Crawford, Travis Lundrigan, Cherif F. Matta, et al. 2013. "Synthesis and characterisation of the unsubstituted dipyrrin and 4,4-dichloro-4-bora-3a,4a-diaza-s-indacene: improved synthesis and functionalisation of the simplest BODIPY framework." Chemical Communications 49(8): 816-818.
    An improved and scalable synthesis of the unsubstituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene framework facilitates access to the previously unreported parent dipyrrin HCl salt, as well as 4,4-dichloro-4-bora-3a,4a- ...

  • Synthesis and Photobiological Activity of Ru(II) Dyads Derived from Pyrrole-2-Carboxylate Thionoesters 

    Deborah A. Smithen, Huimin Yin, Michael H. R. Beh, Marc Hetu, T. Stanley Cameron, Sherri A. McFarland,*and Alison Thompson. (2017). Inorganic Chemistry, 56, 4121-4132. DOI: 10.1021/acs.inorgchem.7b00072

  • Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton - Electron-poor pyrroles exhibit dramatically reduced nucleophilicity 

    Beshara, Cory S., Beth M. Pearce, and Alison Thompson. 2008. "Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton - Electron-poor pyrroles exhibit dramatically reduced nucleophilicity." Canadian Journal of Chemistry-Revue Canadienne De Chimie 86(10): 951-957.
    With the aim of furthering our investigations into the asymmetric complexation of dipyrrinato ligands, a dipyrrin bearing a stereogenic centre directly adjacent to the conjugated skeleton was synthesized. The electron- ...

  • Synthesis of heteroleptic pyrrolide/bipyridyl complexes of ruthenium(II) 

    Lundrigan, Travis, Carla L. M. Jackson, Md Imam Uddin, Lloyd A. Tucker, et al. 2012. "Synthesis of heteroleptic pyrrolide/bipyridyl complexes of ruthenium(II)." Canadian Journal of Chemistry-Revue Canadienne De Chimie 90(8): 693-700.
    The synthesis and characterization of the first heteroleptic pyrrolide/2,2'-bipyridyl complexes of ruthenium(II) are reported. Pyrroles substituted at the 2-position with X = O functionality react with Ru(bipy)(2)Cl-2.2H(2)O ...

  • Synthesis of natural products containing the pyrrolic ring 

    Young, Ian S., Paul D. Thornton, and Alison Thompson. 2010. "Synthesis of natural products containing the pyrrolic ring." Natural Product Reports 27(12): 1801-1839.
    This review provides an overview of the synthetic chemistry that has been utilised to prepare natural products containing a pyrrolic ring.