Document Type
Thesis
Date of Degree Completion
Fall 2020
Degree Name
Master of Science (MS)
Department
Chemistry
Committee Chair
Timothy K. Beng
Second Committee Member
Levente Fabry-Asztalos
Third Committee Member
Carin Thomas-Bradley
Abstract
With intrinsic versatility and an overwhelming presence in natural products, nitrogen- and oxygen-containing heterocycles boast a plethora of medicinal properties. Specifically, lactams and lactones are the respective luminaries of the antibiotic and flavor worlds. However, the synthesis of fused lactams-lactones, especially those bearing trans-fusion, is challenging from the standpoints of chemoselectivity, stereoselectivity, and regioselectivity. In this thesis, the highly-selective, cost-effective, and high-yielding conversion of readily affordable allylic lactams into trans-fused lactam-lactones by intramolecular vicinal difunctionalization is explored. The approach is highly divergent and requires only two steps, which bodes well for the construction of medicinally pertinent fragments. It is anticipated that the aforementioned merits of the methodology will endear it to both the medicinal and synthesis communities.
Recommended Citation
Rodriguez, Morgan J., "Selective Synthesis of Trans-fused Lactam-Lactones by Vicinal Difunctionalization of Readily Affordable Allylic Lactams" (2020). All Master's Theses. 1443.
https://digitalcommons.cwu.edu/etd/1443