Organic Oral Presentations

A Clothing Solution

Dawn, Andrew

  • Andrew Dawn, Chadron M. Friesen*
  • Organization: Trinity Western University
  • Funding: TWU

Abstract: There is an incredible amount of preventable textile waste in North America and the problem is being shipped to the third world. This research focuses on developing a method to chemically recycle these materials. The initial steps, presented here, are investigations into the solubility of cotton and polyester fibres. This work has achieved the dissolution of cotton and polyester in a variety of solvents. Concluding tests were also conducted to analyze the prospect of separating a cotton and polyester blend - of which a majority or textiles are.

Tetrabromotrisbispirobifluorene: Synthesis and Characterisation of a New Light Emitting Copolymer

Edwards, Kale

  • Kale Edwards, Jonathon Veinot*
  • Organization: University of Alberta
  • Funding: NSERC

Abstract: The advancement of display technology is a large driving force in the field of materials chemistry. Polymer light-emitting diodes (PLEDs) are poised to change the face of consumer display technology. These materials have potential to be energy efficient, cost-effective and can be printed onto flexible substrates, opening a world of possibilities. The development of stable light-emitting polymers is a key stepping stone in this progression. Currently, polyfluorenedioctyl (PFO) polymers are one of the industry workhorse materials used to produce blue light, however, PFO polymers are prone to thermal degradation and oxidation resulting in unwanted green emission. My research focuses on the development of a new blue emitting tetrabromotrispirobifluorene/PFO copolymer, a polymer that has potential to be more thermally and oxidatively stable than PFO polymers. The synthesis of the tetrabromotrispirobifluorene monomer and the copolymer (Figure 1) will be presented, along with characterization of their structure and optical properties.

Synthesis of a Bis(isobenzofuran): 1,2-Bis(isobenzofuranyl)ethylene

Hannon, Matthew

  • Matthew Hannon, Michelle Thibault, Peter Dibble*
  • Organization: University of Lethbridge
  • Funding: University of Lethbridge

Abstract: Isobenzofurans (IBF)s, 1, are highly reactive dienes in Diels-Alder reactions and have been found to be useful in the synthesis of natural products, polymers, and cyclophanes. Bis(IBF)s are composed of two reactive IBF moieties connected by different structural elements. Attachment of trialkylsilyl groups such as t-butyldimethylsilyl (TBS) to IBFs decreases their reactivity, thus allowing for the molecule to be stored and used more easily, while retaining the reactive nature of the compound. The silylated version of 2 (3) can be further used in the synthesis of cyclophanes, our target molecules being stilbenophanes, 4. Progress towards the development of Bis(IBF) 3 and related cyclophanes, 4, will be presented.

Fungal Catalysis of Oxymatrine into Matrine

Hrysio, Ursula

  • Ursula Hrysio, Chad Iverson, Ather Ata*
  • Organization: University of Winnipeg
  • Funding: University of Winnipeg

Abstract: Microorganisms are known for their ability to catalyze a large number of oxidative, reductive, conjugative, and degradative reactions of many classes of natural products in a xenobiotic fashion. Most interestingly, common microorganisms can metabolize xenobiotics in a manner remarkably similar to that shown by mammals. This similarity in metabolic profile is largely explained by the presence of the enzyme cytochrome P-450 monooxygenase in these organisms. Microorganisms have been used successfully as in vitro models to mimic and predict the metabolic fate of pharmaceutical agents in mammalian systems. The metabolites obtained through the method often parallel very closely those obtained from human biotrnasformations.

Oxymatrine, an alkaloid isolated from Sophora flavescens, exhibits interesting biological activities including analgesic, anti-inflammatory, anti-viral, and anti-cancer activities. Microbial transformation of oxymatrine using whole cell culture of Penicillium chrysogenum afforded a known alkaloid, matrine. In this presentation, isolation and structure elucidation of matrine will be discussed.

Chemical Constituents of Matricaria chamomilla

Li, Yi-meng

  • Yimeng Li, Chad Iverson, Ather Ata*
  • Organization: University of Winnipeg
  • Funding: University of Winnipeg

Abstract: Matricaria chamomilla, a flowering plant, is native to Europe, but has more recently introduced to North America. This plant is commonly known as chamomile. For thousands of years extracts of this plant have been utilized by folk healers to treat wounds, ulcers, eczema, gout, skin irritations, neuralgia, rheumatic pain, chicken pox, fevers, gastrointestinal upset, and a vast number of other ailments. Recent studies on this plant have shown that the majority of the demonstrated effects of chamomile may be attributed to the high content of terpenes and flavonoids found within this plant. These compounds have been shown to possess antioxidative, antibacterial, antifungal, anti-inflammatory, anticancer, antiallergic, antipyretic, and antispasmodic activities, as well as mild sedative properties. Our recent phytochemical studies on the methanolic extract of M. chamomilla of Manitoban origin resulted in the isolation of several natural products. In this talk, isolation and structure elucidation of these natural products will be discussed.

Phytochemical Studies on Buxus natalensis

Liang, Xi Yi

  • Xi Yi Liang, Wadim Matochko, Abin James, Athar Ata*
  • Organization: University of Winnipeg
  • Funding: University of Winnipeg

Abstract: Plants of genus Buxus are used in folk medicines to cure fatigue, rheumatism, malaria, depression, and skin infections. For instance, the ethanolic extract of B. sempervirens exhibits anti-HIV activity and delayed progression in HIV-infected asymptomatic patients. Previous chemical studies on various species of genus Buxus have resulted in the isolation of over 200 new alkaloids. These alkaloids have shown interesting biological activities. For instance, buxmicrophylline G exhibits cytotoxicity against HepG2 cells with an IC50 value of 0.89 M. Our recent phytochemical studies on B. natalensis resulted in the isolation of several new steroidal alkaloids. In this talk, isolation and structure elucidation with aid of NMR spectroscopic methods of these newly isolated alkaloids will be presented.

Synthesis of a novel branched-chain monosaccharide

Liew, Sean

  • Sean Liew, Li Xia, Todd L. Lowary*
  • Organization: University of Alberta
  • Funding: University of Alberta, NSERC

Abstract: Lipooligosaccharides (LOS) are present on the outer surface of Mycobacterium tuberculosis, which causes tuberculosis. In this presentation, studies on the synthesis of a structural analog of an unusual tetrol-substituted monosaccharide of a LOS will be discussed. The route to the molecule involved the use of previously established chemistry to generate a protected pyranose from 2-acylfuran. Next this substrate was subjected to a range of reactions with the aim of increasing the stereoselectivity of the desired product.


A synthesis for tetrazole functionality from amide precursor

Maillet, Robert

  • Robert Maillet, Chang-Chun Ling*
  • Organization: University of Calgary
  • Funding: University of Calgary, NSERC

Abstract: The synthesis of tetrazole ring systems has been an area of interest for some time, there have been several purposed methods for their synthesis, however never one which resulted from an amide or imidate precursor species. Recent discovery by Y. Cai et. all showed the 5-membered aromatic ring could be formed in this manner. This reaction, and these conditions were tested with multiple substrates and 3 new tetrazole species were identified and characterized. It was also discovered that a key factor to the success of this reaction may be the presence of an extremely hydrophobic or bulky group at either the R1 or R2 position.


An Aza-Wittig Approach to Sulfinimines and Sulfonamindes

Ratiani, Mariam

  • Mariam Ratiani, Bryan Hill*
  • Organization: Brandon University
  • Funding: Brandon University

Abstract: Sulfonamides constitute an important class of medicinally important compounds. There are numerous synthetic routes to sulfonamides available; herein we report our work towards the synthesis of sulfinimines and sulfonamides using an aza-Wittig methodology. Sulfonyl azides are reacted with XR3 to yield RSO2N=XR3 where X = P, As, Sb. These aza-ylides were then reacted with a number of different aldehydes. A one-pot Ruthenium mediated aza-Wittig reaction is also investigated using a sulfonyl azide, RuCl2(PPh3)3 and the various aldehydes in question.

Phytochemical Studies on Drypetes gossweileri

Tan, Damaris

  • Damaris Tan, Wadim Matochko, Athar Ata*
  • Organization: University of Winnipeg
  • Funding: University of Winnipeg

Abstract: The genus Drypetes consists of over 200 species mainly located in West and Central Africa. Plants of this genus are reported to exhibit anti-inflammatory and analgesic properties. Previous, phytochemical studies on Drypetes gossweileri have resulted in the isolation of steroids and flavanoids. Our recent chemical studies on the methanolic extract of the bark of this plant resulted in the isolation of a novel aromatic glycoside, N-beta-glucopyranosyl-p-hydroxyphenyl acetamide and two known aromatic compounds, p-hydroxyphenyl acetic acid and p-hydroxyphenyl acetonitrile. In this presentation, isolation and structure elucidation of these natural products will be discussed.

Porphyrin Synthesis for Light Harvesting Application

Terpstra, Andrea

  • Andrea Terpstra, Todd Sutherland*
  • Organization: University of Calgary
  • Funding: UofC, NSERC, Government of Alberta, CFI

Abstract: A new generation of processable organic semiconductors known as discotic liquid crystals, self-assembled from porphyrins (electron donors) and electron transporters, have potential for the development of inexpensive solar energy sources. The focus of this research is the convergent synthesis of porphyrins containing long C12 alkyl chains. There are two common approaches to form porphyrin 3. The first approach is a one step reaction where 1 is reacted with pyrrole, trifluoroacetic acid and DDQ to form 3 in yields of 1-10%. The second step-wise approach requires the synthesis and isolation of the dipyrrole methane 2, which is condensed with 1 in the presence of a Lewis acid to form 3 in yields of 20-60%. The porphyrins were characterized by standard organic techniques, cyclic voltammetry, differential scanning calorimetry and UV-visible spectroscopy to determine possible liquid crystalline properties. Both 3a, 3b, 3c and 3d demonstrated intense electronic absorptions with molar coefficients in the 4 x 105 M-1•cm-1 range for the free porphyrins and 1 x 105 M-1•cm-1 for the metalloporphyrin indicating strong potential for light harvesting applications. The 2-step process is advantageous because it provides better yields and has the potential to make asymmetric porphyrins, which have more tunability for further applications.