Progress Toward the Total Synthesis of Credneramide A and B
Document Type
Oral Presentation
Campus where you would like to present
SURC Ballroom C/D
Start Date
15-5-2014
End Date
15-5-2014
Keywords
Neuroscience, Organic synthesis
Abstract
In a chemical synapse, the process of synaptic transmission is as follows: when an action potential reaches the axon terminal, it opens voltage-gated calcium channels, allowing calcium ions to enter the terminal. Calcium causes synaptic vesicles filled with neurotransmitter molecules to fuse with the membrane, releasing their contents into the synaptic cleft. The neurotransmitters diffuse across the synaptic cleft and activate receptors on the postsynaptic neuron. High cytosolic calcium in the axon terminal also triggers mitochondrial calcium uptake, which, in turn, activates mitochondrial energy metabolism to produce ATP to support continuous neurotransmission. Many common antidepressants work to inhibit the calcium oscillations in neurons. Two newly discovered natural products, credneramide A and B, were found to inhibit calcium oscillations in cerebrocortical mouse neurons. Phenethylamine, the parent compound of credneramides, targets dopaminergic neurons, resulting in fewer side effects than antidepressants targeting serotonin. We carried out the known reaction between propargylmagnesium bromide and acrolein to assemble 1-hexen-5-yn-3-ol. Then, we lengthened the backbone of the molecule using a chemical reaction known as a Johnson ortho-ester Claisen rearrangement to afford the compound oct-4-en-7-yne ethanoic acid. After these steps have been successfully completed, we will continue the synthesis further, ending with the crednaramide A and B.
Recommended Citation
O'Neal, Kathryn, "Progress Toward the Total Synthesis of Credneramide A and B" (2014). Symposium Of University Research and Creative Expression (SOURCE). 39.
https://digitalcommons.cwu.edu/source/2014/posters/39
Poster Number
17
Additional Mentoring Department
Chemistry
Progress Toward the Total Synthesis of Credneramide A and B
SURC Ballroom C/D
In a chemical synapse, the process of synaptic transmission is as follows: when an action potential reaches the axon terminal, it opens voltage-gated calcium channels, allowing calcium ions to enter the terminal. Calcium causes synaptic vesicles filled with neurotransmitter molecules to fuse with the membrane, releasing their contents into the synaptic cleft. The neurotransmitters diffuse across the synaptic cleft and activate receptors on the postsynaptic neuron. High cytosolic calcium in the axon terminal also triggers mitochondrial calcium uptake, which, in turn, activates mitochondrial energy metabolism to produce ATP to support continuous neurotransmission. Many common antidepressants work to inhibit the calcium oscillations in neurons. Two newly discovered natural products, credneramide A and B, were found to inhibit calcium oscillations in cerebrocortical mouse neurons. Phenethylamine, the parent compound of credneramides, targets dopaminergic neurons, resulting in fewer side effects than antidepressants targeting serotonin. We carried out the known reaction between propargylmagnesium bromide and acrolein to assemble 1-hexen-5-yn-3-ol. Then, we lengthened the backbone of the molecule using a chemical reaction known as a Johnson ortho-ester Claisen rearrangement to afford the compound oct-4-en-7-yne ethanoic acid. After these steps have been successfully completed, we will continue the synthesis further, ending with the crednaramide A and B.
Faculty Mentor(s)
Chamberland, Stephen