Selective Synthesis of Trans-fused Lactam-Lactones by Vicinal Difunctionalization of Readily Affordable Allylic Lactams

<p>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 <em>trans</em>-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 <em>trans</em>-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.</p>

Name thesis:degree_name

Master of Science (MS)

Discipline thesis:degree_discipline

Chemistry

Year dc:date.available

2020

Author dc:creator

• Rodriguez, Morgan J.

Contributors dc:contributor

• Timothy K. Beng
• Levente Fabry-Asztalos
• Carin Thomas-Bradley

• Halolactonization
• Castagnoli-Cushman
• Organic Chemistry

Repository record dc:identifier

https://digitalcommons.cwu.edu/etd/1443

OAI identifier oai:identifier

oai:digitalcommons.cwu.edu:etd-2468