Modular Regio-, Chemo-, and Stereoselective Access to trans-[n,6]-Fused Lactam-Halolactones
Document Type
Poster
Campus where you would like to present
Ellensburg
Event Website
https://digitalcommons.cwu.edu/source
Start Date
15-5-2019
End Date
15-5-2019
Abstract
Both lactam and lactone structures result in a plethora of bioactivities such as anti-Alzheimer, anti-anxiety, and more. Fusion of the two unlocks more bioactivities with the most classic of which being anti-bacterial, as seen in penicillin. However, synthesis of such structures is limited to β- or γ-lactones fused in a cis manner. In this embodiment, an unprecedented approach to transfusion of Δ-halolactones to lactams is described, paving the way for new biochemical exploration. The low-cost and high-yield method is highly chemo-, regio-, and stereoselective and is achieved through one-pot halolactonizations of γ-alkenoic lactamoyl acids resourcefully prepared from cheap feedstock chemicals. The approach is highly amenable to late-stage diversification and high throughput screening studies. It is anticipated that the uniquely meritorious methodology will attract interest in the medicinal and synthesis communities.
Winner, Outstanding Poster Presentation, College of the Sciences.
Recommended Citation
Rodriguez, Morgan, "Modular Regio-, Chemo-, and Stereoselective Access to trans-[n,6]-Fused Lactam-Halolactones" (2019). Symposium Of University Research and Creative Expression (SOURCE). 223.
https://digitalcommons.cwu.edu/source/2019/Posters/223
Department/Program
Chemistry
Modular Regio-, Chemo-, and Stereoselective Access to trans-[n,6]-Fused Lactam-Halolactones
Ellensburg
Both lactam and lactone structures result in a plethora of bioactivities such as anti-Alzheimer, anti-anxiety, and more. Fusion of the two unlocks more bioactivities with the most classic of which being anti-bacterial, as seen in penicillin. However, synthesis of such structures is limited to β- or γ-lactones fused in a cis manner. In this embodiment, an unprecedented approach to transfusion of Δ-halolactones to lactams is described, paving the way for new biochemical exploration. The low-cost and high-yield method is highly chemo-, regio-, and stereoselective and is achieved through one-pot halolactonizations of γ-alkenoic lactamoyl acids resourcefully prepared from cheap feedstock chemicals. The approach is highly amenable to late-stage diversification and high throughput screening studies. It is anticipated that the uniquely meritorious methodology will attract interest in the medicinal and synthesis communities.
Winner, Outstanding Poster Presentation, College of the Sciences.
https://digitalcommons.cwu.edu/source/2019/Posters/223
Faculty Mentor(s)
Timothy Beng