Tony Durst

Synthetic and Medicinal Organic Chemistry;
Organosulfur Compounds;
Natural Product Isolation and Bioassays

  • Position: Professor
  • Education: Ph.D. (Western Ontario)
  • Phone: (613) 562-5800 ext 6072
  • Fax: (613) 562-5170
  • E-Mail: tdurst@science.uottawa.ca

Award:

University of Ottawa Professor of the Year, 1999, for Excellence in Teaching.

Title of award lecture. Building Better Aspirins. From Willow Bark to Enzyme Inhibitors.

Specific Topics:

 
Synthesis of compounds of medicinal interest often using Diels-Alder reactions involving o-quinodimethanes as a key step.
Optically active à-amino acids via dynamic kinetic resolution [DKR]. Synthesis of the ACE inhibitors, Enalapril and Benazapril, via the DKR approach.
Benzyne Chemistry. Synthesis of 2-substuted-iodobenzenes. The formation of these products takes place via iodine ate complexes as intermediates. Development of this reaction type as a route to a variety of substituted benzenes. The preparation of benzocyclobutenonone and-cyclobutenols via the reaction of benzynes and ketone and ester enolates
Natural product chemistry  (jointly with Professor J.T. Arnason, Department of Biology). Topics in this area include (i) isolation and characterization of plant metabolites as insect control agents; (ii) antimalarials derived from extracts of plants native to Cosata Rica and Indonesia; (iii) Evaluation of extracts from members of the Marcgraviaceae family as natural anti-anxiety drugs; Chemical investigation of rare plant species. Currently we are isolating products from a new member of the Canelaceae family recently identified by our botanist colleagues, Luis Poveda and and Pablo Sanchez , at the Universida Nacional Costa Rica [Heredia}
Design and Synthesis of anti-oxidants based on theoretical calculations [Prof. Jim Wright., Carleton University]. Targets include modified versions of Vitamin E, reveratrol [a natural cancer preventative islated from red grapes],  and other 1,2-dihydroxybenzenes. Preparation of  dendrityic anti oxidants.

Recent Publications:

    1. S. Tripathy, H.Hussain and Tony Durst. Iodine Ate Complexes and N-Lithiobenzocyclobutenamine Intermediates in the reactions of alpha-Lithionitriles with Benzynes. Submitted to tetrahedron Letters. May 2000.
    2.   S.Tripathy, R. Leblanc  and T. Durst.  Conversion of Iodobenzenes to 2-substituted iodobenzenes via benzyne intermediates.  Organic Letters, 1999, 1, 1973-1976.
    3. (126)  R. N. Ben and Tony Durst. The synthesis of optically active a-amino esters via dynamic kinetic resolution (DKR): A mechanistic study. J. Org. Chem. 1999, 64,  7700-7706.
    4. A.-S. Belzile, S. L. Majerus, C. Podesfinski, G. Guillet, T. Durst and J. T. Arnason. Dillapiol Derivatives as synergists. Structure-Activity relationships. Pesticide Biol. Biochem. (1999). (Accepted)
    5. S.L. MacKinnon, C. Bensimon, J.T. Arnason, P.E. Vindas-Sanchez and T. Durst.  Spirocaracollitones CD-spirotriterpenoids from Ruptiliocarpon Caracolito.  J. Org. Chem.1997, 62, 840-845.
    6. S.L. MacKinnon, T. Durst, J.T. Arnason, C. Angerhofer, J. Pezzuto, P.E. Sanchez- Vindas, L.J. Proveda, M. Gbeassor.  Antimalerial activity of tropical meliaceae extracts and gedunin derivatives.  J. Nat. Product 1997 60, 336-341
    7. T.J. Connolly and T. Durst.  Photochemically generated bicyclic o-quinodimethanes.  Photoenolization of bicyclic aldehydes and ketones.Tetrahedron. 1997,  53, 15969-15982.
    8. (119) T.J. Connolly and T. Durst.  The synthesis of o-quinodimethanes from tricyclic sulfones.  Tetrahedron. 1997, 53, 15957-15968.