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.

Available for download on Friday, December 16, 2022

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