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Barb Morra

Barb Morra

Academic Title: Assistant Professor, Teaching Stream

Phone: 416-978-3686

Office: 114

Email:

Research

My research interests are mainly within organic chemistry, where my primary focus is the development of new synthetic strategies towards functionalized indole compounds and their application towards the synthesis of natural products. The main objective of my research and teaching program is to provide undergraduate students with the opportunity to apply their chemical knowledge while conducting independent research. Throughout the program, students gain valuable knowledge as they experience every aspect of working in an organic chemistry laboratory. Students will design and execute synthetic strategies while learning the advanced laboratory techniques involved with performing a variety of chemical transformations, including compound purification and elucidation.

The focus of my research program involves studies towards the synthesis of highly functionalized indole products via [2+3] and [3+3] cyclization reactions. The basis of this research begins with the fundamental reactivity of gramine. This naturally occurring indole derivative easily undergoes alkylation and elimination steps to form a very reactive electrophile, which is well known to participate in addition reactions with a variety of nucleophiles (Figure 1).

Figure 1: Gramine reactivity
Figure 1: Gramine reactivity

However, once the addition reaction has taken place, the resulting indole compound has the potential for further reactivity as a nucleophile. My research program will involve exploring potential cyclization reactions where 1,2-dipolarophiles could participate in [2+3] cyclizations, while [3+3] cyclizations could be observed with 1,3-dipolarophiles (Figure 2). These cyclization reactions could give rise to a wide array of 5- and 6-membered ring fused indole compounds.

Figure 2: Cyclization reactions
Figure 2: Cyclization reactions

The development of new synthetic methods for the construction of functionalized indole compounds is of particular interest due to their abundance in biologically active compounds. The application of the [2+3] and [3+3] cyclization reaction strategies developed in my program will ultimately be applied to the synthesis of natural products containing this structural motif (Figure 3).

Figure 3: Indole natural products
Figure 3: Indole natural products